Compound containing 1,3-diene structure and method for producing same

ABSTRACT

Disclosed is a compound containing a divalent group represented by formula (I). (In formula (I), Ar 1  represents an arylene group, a divalent heterocyclic group or a divalent aromatic amine group; J 1  represents a phenylene group; J 2  represents an alkylene group; X represents an oxygen atom or a sulfur atom; j represents 0 or 1, k represents an integer of 0-3, and l represents 0 or 1, while satisfying 1≦j+k+l≦5; m represents 1 or 2; R 1  represents a hydrogen atom, an alkyl group, an alkoxy group, an alkylthio group, an aryl group, an aryloxy group, an arylthio group, an arylalkyl group, an arylalkoxy group, an arylalkylthio group, an arylalkenyl group, an arylalkynyl group, an amino group, a substituted amino group, a silyl group, a substituted silyl group, a halogen atom, an acyl group, an acyloxy group, an imine residue, a carbamoyl group, an acid imide group, a monovalent heterocyclic group, a carboxyl group, a substituted carboxyl group, a cyano group or a nitro group; the plurality of R 1 &#39;s may be the same as or different from each other; and when there are a plurality of J 1 &#39;s, J 2 &#39;s, X&#39;s, j&#39;s, k&#39;s or l&#39;s, the J 1 &#39;s, J 2 &#39;s, X&#39;s, j&#39;s, k&#39;s or l&#39;s may be the same as or different from each other, respectively.)

TECHNICAL FIELD

The present invention relates to a compound containing a 1,3-dienestructure and a method for producing the same.

BACKGROUND ART

A high molecular-weight light-emitting material and a charge transportmaterial are useful as e.g., a material for use in an organic layer of alight-emitting device and thus have been studied in various ways. As thematerial above, for example, a compound that can be hardened bycrosslinking a benzocyclobutene residue for producing a layeredlight-emitting device (Patent Literatures 1 and 2) and a compound havingtwo olefins (non-conjugated diene) useful for producing a layeredlight-emitting device (Patent Literature 3) have been proposed.

CITATION LIST Patent Literature

-   Patent Literature 1: International Publication No. WO2005/049689-   Patent Literature 2: JP 2008-106241 A-   Patent Literature 3: International Publication No. WO2004/093154

SUMMARY OF INVENTION Technical Problem

However, the aforementioned compound is insufficient in harden ability.

In the circumstances, an object of the present invention is to provide acompound showing an excellent harden ability.

Solution to Problem

The present invention firstly provides a compound comprising a divalentgroup represented by the following formula (I):

wherein Ar¹ represents an arylene group, a divalent heterocyclic groupor a divalent aromatic amine group; J¹ represents a phenylene group; J²represents an alkylene group; X represents an oxygen atom or a sulfuratom; j is 0 or 1, k is an integer of 0 to 3 and l is 0 or 1, such thatl≦j+k+l≦5; m is 1 or 2; R¹ represents a hydrogen atom, an alkyl group,an alkoxy group, an alkylthio group, an aryl group, an aryloxy group, anarylthio group, an arylalkyl group, an arylalkoxy group, anarylalkylthio group, an arylalkenyl group, an arylalkynyl group, anamino group, a substituted amino group, a silyl group, a substitutedsilyl group, a halogen atom, an acyl group, an acyloxy group, an imineresidue, a carbamoyl group, an acid imide group, a monovalentheterocyclic group, a carboxyl group, a substituted carboxyl group, acyano group or a nitro group; a plurality of R¹ may be the same ordifferent; and a plurality of J¹, J², X, j, k and l each may be the sameor different.

The present invention secondly provides a composition comprising atleast one selected from the group consisting of a hole transportmaterial, an electron transport material and a light-emitting material,and the aforementioned compound.

The present invention thirdly provides a liquid composition containingthe aforementioned compound and a solvent.

The present invention fourthly provides a film containing theaforementioned compound and a film formed by crosslinking theaforementioned compound.

The present invention fifthly provides a light-emitting device havingelectrodes comprising an anode and a cathode and an organic layerprovided between the electrodes and containing the aforementionedcompound.

The present invention sixthly provides a surface light source and adisplay having the aforementioned light-emitting device.

The present invention seventhly provides an organic transistor andorganic photoelectric transducer formed by using the aforementionedcompound.

The present invention eighthly provides a compound represented by thefollowing formula (X):

wherein Ar¹ is an arylene group, a divalent heterocyclic group or adivalent aromatic amine group; J¹ represents a phenylene group, J²represents an alkylene group; X represents an oxygen atom or a sulfuratom; X¹ and X² each independently represent a halogen atom; k is aninteger of 0 to 3, l is 0 or 1 and m is 1 or 2; and a plurality of J¹,J², X, k and l each may be the same or different.

The present invention ninthly provides a method for producing a compoundrepresented by the above formula (X), comprising reacting, in a base, acompound represented by the following formula (XI):

wherein Ar¹ represents an arylene group, a divalent heterocyclic groupor a divalent aromatic amine group; J¹ represents a phenylene group; Xrepresents an oxygen atom or a sulfur atom; X¹ and X² each independentlyrepresent a halogen atom; k is an integer of 0 to 3, l is 0 or 1 and mis 1 or 2; and a plurality of J¹, X, k and l each may be the same ordifferent, and a compound represented by the following formula (XII):

wherein X³ represents a halogen atom; and J² represents an alkylenegroup.

Advantageous Effects of Invention

The compound of the present invention is a compound showing an excellentharden ability (for example, thermosetting property).

DESCRIPTION OF EMBODIMENTS

The present invention will be more specifically described below. Notethat, in the specification, a diene structure such as a structurerepresented by the following formula:

wherein R¹ is the same as defined above,is expressed by E-form; however, a diene structure may be E-form, Z-formor a mixture thereof.

<Compound>

The compound of the present invention is a compound comprising adivalent group represented by the above formula (I); however, in view ofheat resistance, it is preferably a polymer compound comprising adivalent group represented by the above formula (I) and more preferablya polymer compound having a divalent group represented by the aboveformula (I) as a repeating unit. Furthermore, the compound of thepresent invention, in view of harden ability, may have two or more typesof divalent groups represented by the above formula (I) as a repeatingunit.

Furthermore, the compound of the present invention is preferably apolymer compound in view of the charge transport property andluminescence property of a crosslinked film, and easiness of forming afilm from a solution.

The compound of the present invention may be either a low molecularcompound or a polymer compound. The low molecular compound refers to acompound having a molecular weight of 1×10¹ or more and less than 1×10³.Furthermore, the low molecular compound usually has a single molecularweight. Whereas, a polymer compound refers to a compound having apolystyrene-equivalent number average molecular weight of 1×10³ to1×10⁸. Furthermore, a polymer compound has a molecular-weightdistribution.

In the above formula (I), Ar¹ is preferably an arylene group in view ofdurability; in view of charge transport property, a divalentheterocyclic group is preferred.

In the above formula (I), the arylene group represented by Ar¹, is anatomic group obtained by removing two hydrogen atoms from an aromatichydrocarbon. Examples thereof include an arylene group having acondensed ring and an arylene group to which an independent benzene ringor two or more condensed rings are bonded directly or via a vinylenegroup or the like. The arylene group may have a substituent. Examples ofthe substituent include an alkyl group, an alkoxy group, an alkylthiogroup, an aryl group, an aryloxy group, an arylthio group, an arylalkylgroup, an arylalkoxy group, an arylalkylthio group, an arylalkenylgroup, an arylalkynyl group, an amino group, a substituted amino group,a silyl group, a substituted silyl group, a halogen atom, an acyl group,an acyloxy group, an imine residue, an amide group, an acid imide group,a monovalent heterocyclic group, a carboxyl group, a substitutedcarboxyl group, a cyano group and a nitro group. In view of solubility,fluorescence property, easiness of synthesis and characteristics of thedevice to be obtained, etc. an alkyl group, an alkoxy group, an arylgroup, an aryloxy group, an arylalkyl group, an arylalkoxy group, ahalogen atom or a cyano group is preferable.

In the arylene group represented by Ar¹, the number of carbon atoms of amoiety excluding a substituent is usually 6 to 60 and preferably 6 to20, and the total number of carbon atoms of a moiety including thesubstituent is usually 6 to 100.

Examples of the arylene group represented by Ar¹ include a phenylenegroup (as shown in the following formulas 1 to 3), a naphthalenediylgroup (as shown in the following formulas 4 to 13), an anthracene-diylgroup (as shown in the following formulas 14 to 19), a biphenyl-diylgroup (as shown in the following formulas 20 to 25), a terphenyl-diylgroup (as shown in the following formulas 26 to 28), a condensed ringcompound group (as shown in the following formulas 29 to 35), afluorene-diyl group (as shown in the following formulas 36 to 38) and abenzofluorene-diyl (as shown in the following formulas 39 to 46). Inview of durability, a phenylene group, a naphthalenediyl group, ananthracene-diyl group, a biphenyl-diyl group, a fluorene-diyl group anda benzofluorene-diyl group are preferable; a naphthalenediyl group, ananthracene-diyl group, a biphenyl-diyl group, a fluorene-diyl group anda benzofluorene-diyl group are more preferable; a naphthalenediyl group,an anthracene-diyl group, a fluorene-diyl group and a benzofluorene-diylgroup are further preferable; a fluorene-diyl group and abenzofluorene-diyl group are particularly preferable; and afluorene-diyl group is the most preferable. Furthermore, as the arylenegroup represented by Ar¹, in view of easiness of synthesizing thecompound to be obtained, a phenylene group and a fluorene-diyl group arepreferable, p-phenylene, m-phenylene and 2,7-fluorene-diyl groups aremore preferable, and p-phenylene and 2,7-fluorene-diyl groups areparticularly preferable. Note that the following groups may have asubstituent.

The alkyl group serving as a substituent as mentioned above may be anyone of linear, branched and cyclic alkyl groups and may have asubstituent. Such an alkyl group usually has 1 to 20 carbon atoms.Examples thereof include a methyl group, an ethyl group, a propyl group,an isopropyl group, a butyl group, an isobutyl group, a t-butyl group, apentyl group, a hexyl group, a cyclohexyl group, a heptyl group, anoctyl group, a 2-ethylhexyl group, a nonyl group, a decyl group, a3,7-dimethyloctyl group, a lauryl group, a trifluoromethyl group, apentafluoroethyl group, a perfluorobutyl group, a perfluorohexyl groupand a perfluorooctyl group.

The alkoxy group serving as a substituent as mentioned above may be anyone of linear, branched and cyclic alkoxy groups and may have asubstituent. Such an alkoxy group usually has 1 to 20 carbon atoms.Examples thereof include a methoxy group, an ethoxy group, a propyloxygroup, an isopropyloxy group, a butoxy group, an isobutoxy group, at-butoxy group, a pentyloxy group, a hexyloxy group, a cyclohexyloxygroup, a heptyloxy group, an octyloxy group, a 2-ethylhexyloxy group, anonyloxy group, a decyloxy group, a 3,7-dimethyloctyloxy group, alauryloxy group, a trifluoromethoxy group, a pentafluoroethoxy group, aperfluorobutoxy group, a perfluorohexyloxy group, a perfluorooctyloxygroup, a methoxymethyloxy group and a 2-methoxyethyloxy group.

The alkylthio group serving as a substituent as mentioned above may beany one of linear, branched and cyclic alkylthio groups and may have asubstituent. Such an alkylthio group usually has about 1 to 20 carbonatoms. Specific examples thereof include a methylthio group, anethylthio group, a propylthio group, an isopropylthio group, a butylthiogroup, an isobutylthio group, a t-butylthio group, a pentylthio group, ahexylthio group, a cyclohexylthio group, a heptylthio group, anoctylthio group, a 2-ethylhexylthio group, a nonylthio group, adecylthio group, a 3,7-dimethyloctylthio group, a laurylthio group and atrifluoromethylthio group.

The aryl group serving as a substituent as mentioned above is an atomicgroup, which is obtained by removing a single hydrogen atom from anaromatic hydrocarbon, includes an aryl group having a condensed ring, anaryl group to which an independent benzene ring or two or more condensedrings are bonded directly or via a vinylene group or the like. The arylgroup usually has 6 to 60 carbon atoms and preferably 7 to 48 carbonatoms. Examples thereof include a phenyl group, a C₁ to C₁₂ alkoxyphenylgroup (“C₁ to C₁₂ alkoxy” means that the number of carbon atoms of thealkoxy moiety is 1 to 12. The same is applied hereinafter), a C₁ to C₁₂alkylphenyl group (“C₁ to C₁₂ alkyl” means that the number of carbonatoms of the alkyl moiety is 1 to 12. The same is applied hereinafter),a 1-naphthyl group, a 2-naphthyl group, a 1-anthracenyl group, a2-anthracenyl group, a 9-anthracenyl group and a pentafluorophenylgroup; and preferably a C₁ to C₁₂ alkoxyphenyl group and a C₁ to C₁₂alkylphenyl group.

Examples of the C₁ to C₁₂ alkoxyphenyl group include a methoxyphenylgroup, an ethoxyphenyl group, a propyloxyphenyl group, anisopropyloxyphenyl group, a butoxyphenyl group, an isobutoxyphenylgroup, a t-butoxyphenyl group, a pentyloxyphenyl group, a hexyloxyphenylgroup, a cyclohexyloxyphenyl group, a heptyloxyphenyl group, anoctyloxyphenyl group, a 2-ethylhexyloxyphenyl group, a nonyloxyphenylgroup, a decyloxyphenyl group, a 3,7-dimethyloctyloxyphenyl group and alauryloxyphenyl group.

Examples of the C₁ to C₁₂ alkylphenyl group include a methylphenylgroup, an ethylphenyl group, a dimethylphenyl group, a propylphenylgroup, a mesityl group, a methylethylphenyl group, an isopropylphenylgroup, a butylphenyl group, an isobutylphenyl group, a t-butylphenylgroup, a pentylphenyl group, an isoamylphenyl group, a hexylphenylgroup, a heptylphenyl group, an octylphenyl group, a nonylphenyl group,a decylphenyl group and a dodecylphenyl group.

The aryloxy group serving as a substituent as mentioned above usuallyhas 6 to 60 carbon atoms and preferably 7 to 48 carbon atoms. Examplesof the aryloxy group include a phenoxy group, a C₁ to C₁₂ alkoxyphenoxygroup, a C₁ to C₁₂ alkylphenoxy group, a 1-naphthyloxy group, a2-naphthyloxy group and a pentafluorophenyloxy group; and preferably aC₁ to C₁₂ alkoxyphenoxy group and a C₁ to C₁₂ alkylphenoxy group.

Examples of the C₁ to C₁₂ alkoxyphenoxy group include a methoxyphenoxygroup, an ethoxyphenoxy group, a propyloxyphenoxy group, anisopropyloxyphenoxy group, a butoxyphenoxy group, an isobutoxyphenoxygroup, a t-butoxyphenoxy group, a pentyloxyphenoxy group, ahexyloxyphenoxy group, a cyclohexyloxyphenoxy group, a heptyloxyphenoxygroup, an octyloxyphenoxy group, a 2-ethylhexyloxyphenoxy group, anonyloxyphenoxy group, a decyloxyphenoxy group, a3,7-dimethyloctyloxyphenoxy group and a lauryloxyphenoxy group.

Examples of the C₁ to C₁₂ alkylphenoxy group include a methylphenoxygroup, an ethylphenoxy group, a dimethylphenoxy group, a propylphenoxygroup, a 1,3,5-trimethylphenoxy group, a methylethylphenoxy group, anisopropylphenoxy group, a butylphenoxy group, an isobutylphenoxy group,a t-butylphenoxy group, a pentylphenoxy group, an isoamylphenoxy group,a hexylphenoxy group, a heptylphenoxy group, an octylphenoxy group, anonylphenoxy group, a decylphenoxy group and a dodecylphenoxy group.

The arylthio group serving as a substituent as mentioned above may havea substituent on the aromatic ring and usually has about 3 to 60 carbonatoms. Specific examples thereof include a phenylthio group, a C₁ to C₁₂alkoxyphenylthio group, a C₁ to C₁₂ alkylphenylthio group, a1-naphthylthio group, a 2-naphthylthio group and a pentafluorophenylthiogroup.

The arylalkyl group serving as a substituent as mentioned above may havea substituent and usually has about 7 to 60 carbon atoms. Specificexamples thereof include a phenyl-C₁ to C₁₂ alkyl group, a C₁ to C₁₂alkoxyphenyl-C₁ to C₁₂ alkyl group, a C₁ to C₁₂ alkylphenyl-C₁ to C₁₂alkyl group, a 1-naphthyl-C₁ to C₁₂ alkyl group and a 2-naphthyl-C₁ toC₁₂ alkyl group.

The arylalkoxy group serving as a substituent as mentioned above mayhave a substituent and usually has about 7 to 60 carbon atoms. Specificexamples thereof include a phenyl-C₁ to C₁₂ alkoxy group, a C₁ to C₁₂alkoxyphenyl-C₁ to C₁₂ alkoxy group, a C₁ to C₁₂ alkylphenyl-C₁ to C₁₂alkoxy group, a 1-naphthyl-C₁ to C₁₂ alkoxy group and a 2-naphthyl-C₁ toC₁₂ alkoxy group.

The arylalkylthio group serving as a substituent as mentioned above mayhave a substituent and usually has about 7 to 60 carbon atoms. Specificexamples thereof include a phenyl-C₁ to C₁₂ alkylthio group, a C₁ to C₁₂alkoxyphenyl-C₁ to C₁₂ alkylthio group, a C₁ to C₁₂ alkylphenyl-C₁ toC₁₂ alkylthio group, a 1-naphthyl-C₁ to C₁₂ alkylthio group and a2-naphthyl-C₁ to C₁₂ alkylthio group.

The arylalkenyl group serving as a substituent as mentioned aboveusually has about 8 to 60 carbon atoms. Specific examples thereofinclude a phenyl-C₂ to C₁₂ alkenyl group, a C₁ to C₁₂ alkoxyphenyl-C₂ toC₁₂ alkenyl group, a C₁ to C₁₂ alkylphenyl-C₂ to C₁₂ alkenyl group, a1-naphthyl-C₂ to C₁₂ alkenyl group and a 2-naphthyl-C₂ to C₁₂ alkenylgroup. A C₁ to C₁₂ alkoxyphenyl-C₂ to C₁₂ alkenyl group and a C₁ to C₁₂alkylphenyl-C₂ to C₁₂ alkenyl group are preferable.

The arylalkynyl group serving as a substituent as mentioned aboveusually has about 8 to 60 carbon atoms. Specific examples thereofinclude a phenyl-C₂ to C₁₂ alkynyl group, a C₁ to C₁₂ alkoxyphenyl-C₂ toC₁₂ alkynyl group, a C₁ to C₁₂ alkylphenyl-C₂ to C₁₂ alkynyl group, a1-naphthyl-C₂ to C₁₂ alkynyl group and a 2-naphthyl-C₂ to C₁₂ alkynylgroup. A C₁ to C₁₂ alkoxyphenyl-C₂ to C₁₂ alkynyl group and a C₁ to C₁₂alkylphenyl-C₂ to C₁₂ alkynyl group are preferable.

The substituted amino group serving as a substituent as mentioned abovemay be an amino group substituted with one or two groups selected froman alkyl group, an aryl group, an arylalkyl group and a monovalentheterocyclic group. The alkyl group, aryl group, arylalkyl group ormonovalent heterocyclic group may have a substituent. The number ofcarbon atoms of the substituted amino group excluding the number ofcarbon atoms of a substituent is usually about 1 to 60 and preferably 2to 48 carbon atoms.

Specific examples thereof include a methylamino group, a dimethylaminogroup, an ethylamino group, a diethylamino group, a propylamino group, adipropylamino group, an isopropylamino group, a diisopropylamino group,a butylamino group, an s-butylamino group, an isobutylamino group, at-butylamino group, a pentylamino group, a hexylamino group, acyclohexylamino group, a heptylamino group, an octylamino group, a2-ethylhexylamino group, a nonylamino group, a decylamino group, a3,7-dimethyloctylamino group, a laurylamino group, a cyclopentylaminogroup, a dicyclopentylamino group, a dicyclohexylamino group, apyrrolidyl group, a piperidyl group, a ditrifluoromethylamino group, aphenylamino group, a diphenylamino group, a C₁ to C₁₂ alkoxyphenylaminogroup, a di(C₁ to C₁₂ alkoxyphenyl)amino group, a di(C₁ to C₁₂alkylphenyl)amino group, a 1-naphthylamino group, a 2-naphthylaminogroup, a pentafluorophenylamino group, a pyridylamino group, apyridazinylamino group, a pyrimidylamino group, a pyrazylamino group, atriazylamino group, a phenyl-C₁ to C₁₂ alkylamino group, a C₁ to C₁₂alkoxyphenyl-C₁ to C₁₂ alkylamino group, a C₁ to C₁₂ alkylphenyl-C₁ toC₁₂ alkylamino group, a di(C₁ to C₁₂ alkoxyphenyl-C₁ to C₁₂ alkyl)aminogroup, a di(C₁ to C₁₂ alkylphenyl-C₁ to C₁₂ alkyl)amino group, a1-naphthyl-C₁ to C₁₂ alkylamino group and a 2-naphthyl-C₁ to C₁₂alkylamino group.

The substituted silyl group serving as a substituent as mentioned abovemay be a silyl group substituted with 1, 2 or 3 groups selected from analkyl group, an aryl group, an arylalkyl group and a monovalentheterocyclic group. The number of carbon atoms of the substituted silylgroup is usually about 1 to 60 and preferably 3 to 48. Note that thealkyl group, aryl group, arylalkyl group or monovalent heterocyclicgroup may have a substituent.

Specific examples thereof include a trimethylsilyl group, atriethylsilyl group, a tripropylsilyl group, a tri-isopropylsilyl group,a dimethyl-isopropylsilyl group, a diethyl-isopropylsilyl group, at-butyldimethylsilyl group, a pentyldimethylsilyl group, ahexyldimethylsilyl group, a heptyldimethylsilyl group, anoctyldimethylsilyl group, a 2-ethylhexyl-dimethylsilyl group, anonyldimethylsilyl group, a decyldimethylsilyl group, a3,7-dimethyloctyl-dimethylsilyl group, a lauryldimethylsilyl group, aphenyl-C₁ to C₁₂ alkylsilyl group, a C₁ to C₁₂ alkoxyphenyl-C₁ to C₁₂alkylsilyl group, a C₁ to C₁₂ alkylphenyl-C₁ to C₁₂ alkylsilyl group, a1-naphthyl-C₁ to C₁₂ alkylsilyl group, a 2-naphthyl-C₁ to C₁₂ alkylsilylgroup, a phenyl-C₁ to C₁₂ alkyldimethylsilyl group, a triphenylsilylgroup, a tri-p-xylylsilyl group, a tribenzylsilyl group, adiphenylmethylsilyl group, a t-butyldiphenylsilyl group and adimethylphenylsilyl group.

Examples of a halogen atom serving as a substituent as mentioned aboveinclude a fluorine atom, a chlorine atom, a bromine atom and an iodineatom.

The acyl group serving as a substituent as mentioned above usually hasabout 2 to 20 carbon atoms and preferably 2 to 18 carbon atoms. Specificexamples thereof include an acetyl group, a propionyl group, a butyrylgroup, an isobutyryl group, a pivaloyl group, a benzoyl group, atrifluoroacetyl group and a pentafluorobenzoyl group.

The acyloxy group serving as a substituent as mentioned above usuallyhas about 2 to 20 carbon atoms and preferably 2 to 18 carbon atoms.Specific examples thereof include an acetoxy group, a propionyloxygroup, a butyryloxy group, an isobutyryloxy group, a pivaloyloxy group,a benzoyloxy group, a trifluoroacetyloxy group and apentafluorobenzoyloxy group.

The imine residue serving as a substituent as mentioned above refers toa residue obtained by removing a single hydrogen atom from an iminecompound (which refers to an organic compound having —N═C— in themolecule. Examples thereof include aldimine, ketimine and a compoundobtained by substituting a hydrogen atom on N of these with e.g., analkyl group) and usually has about 2 to 20 carbon atoms and preferably 2to 18 carbon atoms. Specific examples include groups represented by thefollowing structural formulas.

The carbamoyl group serving as a substituent as mentioned above usuallyhas about 2 to 20 carbon atoms and preferably 2 to 18 carbon atoms.Specific examples thereof include a formamide group, an acetamide group,a propioamide group, a butyroamide group, a benzamide group, atrifluoroacetamide group, a pentafluorobenzamide group, a diformamidegroup, a diacetamide group, a dipropioamide group, a dibutyroamidegroup, a dibenzamide group, a ditrifluoroacetamide group and adipentafluorobenzamide group.

Examples of the acid imide group serving as a substituent as mentionedabove include a residue obtained by removing a hydrogen atom bound tothe nitrogen atom of the acid imide and having about 4 to 20 carbonatoms. Specific examples thereof include the groups shown below.

The monovalent heterocyclic group serving as a substituent as mentionedabove refers to a remaining atomic group obtained by removing a singlehydrogen atom from a heterocyclic compound and usually having about 4 to60 carbon atoms and preferably 4 to 20 carbon atoms. Of the monovalentheterocyclic groups, a monovalent aromatic heterocyclic group ispreferable. Note that the number of carbon atoms of a substituent is notincluded in the number of carbon atoms of a heterocyclic group. Theheterocyclic compound herein refers to an organic compound having a ringstructure, which is not only constituted of a carbon atom but alsocontains a hetero atom such as oxygen, sulfur, nitrogen, phosphorus andboron, within the ring. Specific examples thereof include a thienylgroup, a C₁ to C₁₂ alkylthienyl group, a pyrrolyl group, a furyl group,a pyridyl group, a C₁ to C₁₂ alkylpyridyl group, a piperidyl group, aquinolyl group and an isoquinolyl group. A thienyl group, a C₁ to C₁₂alkyl thienyl group, a pyridyl group and a C₁ to C₁₂ alkyl pyridyl groupare preferable.

Examples of the substituted carboxyl group serving as a substituent asmentioned above refers to a carboxyl group substituted with an alkylgroup, an aryl group, an arylalkyl group or a monovalent heterocyclicgroup and usually having about 2 to 60 carbon atoms and preferably 2 to48 carbon atoms. Specific examples thereof include a methoxycarbonylgroup, an ethoxycarbonyl group, a propoxycarbonyl group, anisopropoxycarbonyl group, a butoxycarbonyl group, an isobutoxycarbonylgroup, a t-butoxycarbonyl group, a pentyloxycarbonyl group, ahexyloxycarbonyl group, a cyclohexyloxycarbonyl group, aheptyloxycarbonyl group, an octyloxycarbonyl group, a2-ethylhexyloxycarbonyl group, a nonyloxycarbonyl group, adecyloxycarbonyl group, a 3,7-dimethyloctyloxycarbonyl group, adodecyloxycarbonyl group, a trifluoromethoxycarbonyl group, apentafluoroethoxycarbonyl group, a perfluorobutoxycarbonyl group, aperfluorohexyloxycarbonyl group, a perfluorooctyloxycarbonyl group, aphenoxycarbonyl group, a naphthoxycarbonyl group and apyridyloxycarbonyl group. Note that the alkyl group, aryl group,arylalkyl group or monovalent heterocyclic group may have a substituent.The number of carbon atoms of the substituent is not included in thenumber of carbon atoms of the substituted carboxyl group.

In the above formula (I), the divalent heterocyclic group represented byAr¹ refers to the remaining atomic group obtained by removing twohydrogen atoms from a heterocyclic compound. The divalent heterocyclicgroup may have a substituent.

The heterocyclic compound refers to an organic compound having a ringstructure, which is not only constituted of a carbon atom but alsocontains a hetero atom such as oxygen, sulfur, nitrogen, phosphorus,boron and arsenic within a ring. As the divalent heterocyclic group, adivalent aromatic heterocyclic group is preferable. As the substituent,in view of solubility of, fluorescence property of, easiness ofsynthesizing the compound to be obtained and characteristic of thedevice to be obtained, etc., an alkyl group, an alkoxy group, an arylgroup, an aryloxy group, an arylalkyl group, an arylalkoxy group, ahalogen atom or cyano group is preferable. These groups and atoms aredefined as described above.

In the divalent heterocyclic group represented by Ar¹, the number ofcarbon atoms of the moiety excluding a substituent is usually, 3 to 60and the total number of carbon atoms including a substituent is usually3 to 100.

Examples of the divalent heterocyclic group represented by Ar¹ includethe following groups. Note that the following groups may have asubstituent.

Divalent heterocyclic group containing a nitrogen atom as a hetero atom:a pyridine-diyl group (as shown in the following formulas 101 to 104), adiazaphenylene group (as shown in the following formulas 105 to 108), atriazine-diyl group (as shown in the following formula 109), aquinoline-diyl group (as shown in the following formulas 110 to 114), aquinoxaline-diyl group (as shown in the following formulas 115 to 119),an acridinediyl group (the following formulas 120 to 123), abipyridyl-diyl group (the following formulas 124 to 126), aphenanthroline diyl group (the following formulas 127 and 128).

A group containing an oxygen atom, a sulfur atom, a nitrogen atom, asilicon atom, etc. as a hetero atom and having a fluorene structure (asshown in the following formulas 129 to 136).

A 5-membered heterocyclic group containing an oxygen atom, a sulfuratom, a nitrogen atom and a silicon atom, etc. as a hetero atom (asshown in the following formulas 137 to 140).

A 5-membered condensed heterocyclic group containing an oxygen atom, asulfur atom, a nitrogen atom and a silicon atom, etc. as a hetero atom(as shown in the following formulas 141 to 158).

A 5-membered heterocyclic group containing an oxygen atom, a sulfuratom, a nitrogen atom and a silicon atom, etc. as a hetero atom andbound at the a position of the hetero atom to form a dimer or anoligomer (as shown in the following formulas 159 to 160).

A 5-membered heterocyclic group containing an oxygen atom, a sulfuratom, a nitrogen atom and a silicon atom, etc. as a hetero atom andbound at the a position of the hetero atom to a phenyl group (as shownin the following formulas 161 to 166).

A 5-membered condensed heterocyclic group containing an oxygen atom, asulfur atom and a nitrogen atom, etc. as a hetero atom and substitutedwith a phenyl group, a furyl group, a thienyl group (the followingformulas 167 to 172).

A 6-membered heterocyclic group containing an oxygen atom and nitrogenatom as a hetero atom (as shown in the following formulas 173-176).

The divalent heterocyclic group represented by Ar¹ is, in view of chargetransport property, preferably a divalent group represented by thefollowing formula (II):

wherein Y represents an oxygen atom, a sulfur atom, —N(R²²)—,—O—C(R²³)(R²⁴)—, or —Si(R²⁵)(R²⁶)—; R²², R²³, R²⁴, R²⁵ and R²⁶ eachindependently represent a hydrogen atom, an alkyl group, an alkoxygroup, an aryl group or an arylalkyl group; and the formula may have asubstituent.

When the above formula (II) has a substituent, examples of thesubstituent include an alkyl group, an alkoxy group, an aryl group, anaryloxy group, an arylalkyl group and an arylalkoxy group. These groupsare the same as defined above.

In the above formula (II), in view of easiness of synthesizing thecompound of the present invention, Y is preferably an oxygen atom, asulfur atom and —N(R²²)— and more preferably an oxygen atom and—N(R²²)—.

A divalent group represented by the above formula (II) is preferably adivalent group represented by the following formula (II)-1 or thefollowing formula (II)-2, since a particularly high charge transportproperty can be obtained.

wherein Y¹ represents an oxygen atom, a sulfur atom, —N(R²²)—,—O—C(R²³)(R²⁴)— or —Si(R²⁵)(R²⁶)—; and the formula may have asubstituent.

wherein Y² represents an oxygen atom, a sulfur atom, —N(R²²)—,—O—C(R²³)(R²⁴)— or —Si(R²⁵)(R²⁶)—; and the formula may have asubstituent.

When the above formulas (II)-1 and (II)-2 have a substituent, examplesof the substituent include an alkyl group, an alkoxy group, an arylgroup, an aryloxy group, an arylalkyl group and an arylalkoxy group.These groups are the same as defined above.

In the above formula (II)-1, in view of easiness of synthesizing thecompound of the present invention, Y¹ is preferably an oxygen atom, asulfur atom, or —N(R²²)—, more preferably an oxygen atom or —N(R²²)— andparticularly preferably an oxygen atom.

In the above formula (II)-2, in view of easiness of synthesizing thecompound of the present invention, Y² is preferably an oxygen atom, asulfur atom or —N(R²²)—, more preferably a sulfur atom or —N(R²²)— andparticularly preferably —N(R²²)—.

The divalent aromatic amine group represented by Ar¹ refers to theremaining atomic group obtained by removing two hydrogen atoms from anaromatic amine, having usually 5 to 100 carbon atoms and preferably 15to 60 carbon atoms. The divalent aromatic amine group may have asubstituent. Note that the number of carbon atoms of a substituent isnot included in the number of carbon atoms of an aromatic amine. Thesubstituent is, in view of solubility of, fluorescence property of andeasiness of synthesizing the compound to be obtained, and easiness ofcrosslinking a film, preferably an alkyl group, an alkoxy group, an arylgroup, an aryloxy group, an arylalkyl group, an arylalkoxy group, ahalogen atom and cyano group. These groups and atoms are the same asdefined above.

Examples of the divalent aromatic amine group represented by Ar¹ includedivalent groups represented by the following formulas 201 to 210. Notethat the following groups may have a substituent.

The divalent aromatic amine group represented by Ar¹ is, in view of holetransport property, preferably a divalent group represented by thefollowing formula (III):

wherein R³ represents a hydrogen atom, an alkyl group, an alkoxy groupor a substituted amino group; and five R³ may be the same or different,or a divalent group represented by the following formula (IV):

wherein R⁴ represents a hydrogen atom, an alkyl group, an alkoxy groupor a substituted amino group; and ten R⁴ may be the same or different.

In the above formulas (III) and (IV), the alkyl group and alkoxy grouprepresented by R³ and R⁴ are the same as defined above.

In the above formulas (III) and (IV), as the substituted amino grouprepresented by R³ and R⁴, an amino group substituted with one or twogroups selected from an alkyl group, an aryl group, an arylalkyl groupand a monovalent heterocyclic group. The alkyl group, aryl group,arylalkyl group and monovalent heterocyclic group may have asubstituent. The number of carbon atoms of the substituted amino groupexcluding the number of carbon atoms of the substituent is usually 1 to60 and preferably 2 to 48.

The substituted amino groups represented by R³ and R⁴ are the same asdefined above.

In the above formula (I), the phenylene group represented by J¹ may havea substituent. Examples of the phenylene group include an o-phenylene,m-phenylene and p-phenylene. Examples of the substituent include analkyl group, an alkoxy group, a halogen atom and a cyano group. Thesegroups are the same as defined above.

In the above formula (I), the alkylene group represented by J² may be alinear or branched group. Examples of the alkyllene group includemethylene, 1,2-ethylene, 1,3-propylene, 1,3-butylene, 1,4-butylene,1,3-pentylene, 1,4-pentylene, 1,5-pentylene, 1,4-hexylene, 1,6-hexylene,1,7-heptylene, 1,6-octylene and 1,8-octylene.

In the above formula (I), X is, in view of easiness of synthesizing thecompound of the present invention, preferably an oxygen atom.

In the above formula (I), in view of easiness of synthesizing thecompound, j is 0 or 1 and particularly preferably 1, of the presentinvention.

In the above formula (I), in view of easiness of synthesizing thecompound of the present invention, k is preferably an integer selectedfrom 0 to 2 and further preferably 0 or 1.

In the above formula (I), the alkyl group, alkoxy group, alkylthiogroup, aryl group, aryloxy group, arylthio group, arylalkyl group,arylalkoxy group, arylalkylthio group, arylalkenyl group, arylalkynylgroup, amino group, substituted amino group, silyl group, substitutedsilyl group, halogen atom, acyl group, acyloxy group, imine residue,carbamoyl group, acid imide group, monovalent heterocyclic group,carboxyl group, substituted carboxyl group, cyano group and nitro grouprepresented by R¹ are the same as defined above. However, in view ofharden ability, a hydrogen atom, an alkyl group, an alkoxy group, ahalogen atom, a nitro group and a cyano group are preferable; a hydrogenatom, an alkyl group, an aryl group and a halogen atom are morepreferable; a hydrogen atom and an alkyl group are further preferable;and a hydrogen atom is particularly preferable.

Furthermore, substituent R¹ may be mutually bound to form rings.

Examples of the ring include a C₁ to C₁₀ cycloalkyl ring that may have asubstituent, a C₁ to C₁₀ cycloalkenyl ring that may have a substituent,a C₆ to C₁₄ aromatic hydrocarbon ring that may have a substituent and aC₄ to C₁₄ heterocyclic ring that may have a substituent.

Examples of the cycloalkyl ring include cyclobutane, cyclopentane,cyclohexane, cycloheptane, cyclooctane, cyclononane and cyclodecane.

Examples of the cycloalkenyl ring include a cycloalkenyl ring having twoor more double bonds. Specific examples thereof include a cyclohexenering, a cyclohexadiene ring and a cyclooctatriene ring.

Examples of the aromatic hydrocarbon ring include a benzene ring, anaphthalene ring and an anthracene ring.

Examples of the heterocyclic ring include a furan ring, atetrahydrofuran ring, a thiophene ring, a tetrahydrothiophene ring, anindole ring, a tetrahydroindole ring, an isoquinoline ring, a pyridinering, a thiazole ring and an oxazole ring.

In the above formula (I), a group represented by the following formula(Ia):

wherein j, k, l, J¹, J² and R¹ are the same as defined above,is, in view of harden ability of the compound of the present invention,preferably a group represented by the following formula (Ib):

wherein k, l, J² and R¹ are the same as defined above,and more preferably a group represented by the following formula (Ic):

wherein k, l and J² are the same as defined above,and a group represented by the following formula (Id):

wherein k, l and J² are the same as defined above.

As the divalent group represented by the above formula (I), divalentgroups represented by the following formulas (I-1) to (I-35) arementioned.

When the compound of the present invention is a polymer compound, inview of easiness of synthesizing the polymer compound, the compound ofthe present invention is preferably a polymer compound having, as thegroup represented by the above formula (I), a repeating unit representedby the following formula (V):

wherein J¹, J², X, R¹, k, l and m are the same as defined above; and R²represents an alkyl group, an aryl group, an arylalkyl group or anarylalkoxy group.

In the above formula (V), the alkyl group, aryl group, arylalkyl groupand arylalkoxy group represented by R² are the same as defined above.

When the compound of the present invention is a polymer compound, inview of harden ability of the polymer compound, the compound of thepresent invention may further have a repeating unit containing acrosslinking group.

The crosslinking group refers to a substituent inducing a crosslinkingreaction by stimulation of heat or light.

Examples of the crosslinking group include an oxiranyl group, anoxetanyl group, a cinnamoyl group, a dienophile group and an alkynylgroup.

When the compound of the present invention is a polymer compound, inview of harden ability, the polymer compound preferably has, in additionto a repeating unit represented by the above formula (I), a repeatingunit represented by the following formula (A):

wherein Ar² represents an arylene group, a divalent heterocyclic groupor a divalent aromatic amine group; J³ represents a direct bond, analkylene group or a phenylene group; and n represents 1 or 2; and aplurality of J³ may be the same or different.

In the above formula (A), the arylene group, divalent heterocyclic groupand divalent aromatic amine group represented by Ar² are the same asdefined above. As Ar², in view of easiness of synthesizing the compoundof the present invention, an arylene group and a divalent heterocyclicgroup are preferable, an arylene group is more preferable, afluorene-diyl group is further preferable and a 2,7-fluorene-diyl groupis particularly preferable.

In the above formula (A), the alkylene group and phenylene grouprepresented by J³ are the same as defined above.

In the group represented by the above formula (A), it is particularlypreferable that Ar² is an arylene group, J³ is a direct bond and n is 2.

When the compound of the present invention is a polymer compound, thepolymer compound preferably contains, in view of harden ability, inaddition to the repeating unit represented by the above formula (I), arepeating unit represented by the following formula (B):

wherein Ar³ represents an arylene group, a divalent heterocyclic groupor a divalent aromatic amine group; J⁴ represents a direct bond, analkylene group or a phenylene group; R⁵ represents a hydrogen atom, analkyl group, an alkoxy group, an alkylthio group, an aryl group, anaryloxy group, an arylthio group, an arylalkyl group, an arylalkoxygroup, an arylalkylthio group, an arylalkenyl group, an arylalkynylgroup, an amino group, a substituted amino group, a silyl group, asubstituted silyl group, a halogen atom, an acyl group, an acyloxygroup, an imine residue, a carbamoyl group, an acid imide group, amonovalent heterocyclic group, a carboxyl group, a substituted carboxylgroup, a cyano group or a nitro group; o represents 1 or 2; a pluralityof R⁵ may be the same or different; and a plurality of J⁴ may be thesame or different.

In the above formula (B), the arylene group, divalent heterocyclic groupand divalent aromatic amine group represented by Ar³ may be the same asdefined above. As Ar³, in view of easiness of synthesizing the compoundof the present invention, an arylene group and a divalent heterocyclicgroup are preferable, an arylene group is more preferable, afluorene-diyl group is further preferable and 2,7-fluorene-diyl group isparticularly preferable.

In the above formula (B), the alkylene group and phenylene grouprepresented by J⁴ are the same as defined above.

In the above formula (B), the alkyl group, alkoxy group, alkylthiogroup, aryl group, aryloxy group, arylthio group, arylalkyl group,arylalkoxy group, arylalkylthio group, arylalkenyl group, arylalkynylgroup, amino group, substituted amino group, silyl group, substitutedsilyl group, halogen atom, acyl group, acyloxy group, imine residue,carbamoyl group, acid imide group, monovalent heterocyclic group,carboxyl group, substituted carboxyl group, cyano group or nitro grouprepresented by R⁵ is the same as defined above. As R⁵, in view of hardenability of the compound of the present invention, a hydrogen atom and ahalogen atom are preferable and a hydrogen atom is more preferable.

In the group represented by the above formula (B), it is particularlypreferable that Ar^(a) is an arylene group, J⁴ is an alkylene group ando is 2.

When the compound of the present invention is a polymer compound, inview of charge transport property of the polymer compound, the compoundof the present invention further preferably contains, in addition to therepeating unit represented by the above formula (I), a repeating unitrepresented by the following formula (C):

wherein R⁶ represents an alkyl group, an aryl group, an arylalkyl groupor an arylalkoxy group; and two R⁶ may be the same or different.

In the above formula (C), the alkyl group, aryl group, arylalkyl groupand arylalkoxy group represented by R⁶ are the same as defined above. AsR⁶, in view of easiness of synthesizing a raw-material monomer, an alkylgroup or an aryl group is preferable and an alkyl group is furtherpreferable.

When the compound of the present invention is a polymer compound, thepolymer compound may have, in view of hole transport property, inaddition to the repeating unit represented by the above formula (I), oneor more repeating unit selected from the group consisting of repeatingunits represented by the following formula (D) and repeating unitsrepresented by the following formula (E).

wherein Ar³, Ar⁴, Ar⁵ and Ar⁶ each independently represent an arylenegroup or a divalent heterocyclic group; Ar⁷, Ar⁸ and Ar⁹ eachindependently represent an aryl group or a monovalent heterocyclicgroup; α and β each independently represent 0 or 1; and Ar³, Ar⁴, Ar⁵,Ar⁶, Ar⁷, Ar⁸ and Ar⁹ may have a substituent.

wherein ring P and ring Q each independently represent an aromatichydrocarbon ring; X³ represents a single bond, an oxygen atom and asulfur atom; and R¹⁰⁰ represents an alkyl group, an alkoxy group, analkylthio group, an aryl group, an aryloxy group, an arylthio group, anarylalkyl group, an arylalkoxy group, an arylalkylthio group, anarylalkenyl group, an arylalkynyl group, an amino group, a substitutedamino group, a silyl group, a substituted silyl group, a halogen atom,an acyl group, an acyloxy group, an imine residue, a carbamoyl group, anacid imide group, a monovalent heterocyclic group, a carboxyl group, asubstituted carboxyl group, a cyano group or a nitro group.

In the above formula (D), the arylene group, divalent heterocyclicgroup, aryl group and monovalent heterocyclic group are the same asdefined above.

Examples of the substituent that Ar³, Ar⁴, Ar⁵, Ar⁶, Ar⁷, Ar⁸ and Ar⁹may have include an alkyl group, an alkoxy group, an alkylthio group, anaryl group, an aryloxy group, an arylthio group, an arylalkyl group, anarylalkoxy group, an arylalkylthio group, an arylalkenyl group, anarylalkynyl group, an amino group, a substituted amino group, a silylgroup, a substituted silyl group, a halogen atom, an acyl group, anacyloxy group, an imine residue, a carbamoyl group, an acid imide group,a monovalent heterocyclic group, a carboxyl group, a substitutedcarboxyl group, a cyano group and a nitro group.

The alkyl group, alkoxy group, alkylthio group, aryl group, aryloxygroup, arylthio group, arylalkyl group, arylalkoxy group, arylalkylthiogroup, arylalkenyl group, arylalkynyl group, amino group, substitutedamino group, silyl group, substituted silyl group, halogen atom, acylgroup, acyloxy group, imine residue, carbamoyl group, acid imide group,monovalent heterocyclic group, carboxyl group, substituted carboxylgroup, cyano group and nitro group are the same as defined above.

In the above formula (E), the aromatic hydrocarbon ring represents anaromatic hydrocarbon ring obtained by removing two bonds from an arylenegroup as mentioned above.

In the above formula (E), the alkyl group, alkoxy group, alkylthiogroup, aryl group, aryloxy group, arylthio group, arylalkyl group,arylalkoxy group, arylalkylthio group, arylalkenyl group, arylalkynylgroup, amino group, substituted amino group, silyl group, substitutedsilyl group, halogen atom, acyl group, acyloxy group, imine residue,carbamoyl group, acid imide group, monovalent heterocyclic group,carboxyl group, substituted carboxyl group, cyano group and nitro groupare the same as defined above.

The repeating unit represented by the above formula (D) is, in view ofhole transport property, preferably a repeating unit represented by thefollowing formula (D)-1 or (D)-2.

wherein R⁷ represents a hydrogen atom, an alkyl group or an alkoxygroup; and three R⁷ may be the same or different.

wherein R⁸ represents a hydrogen atom, an alkyl group or an alkoxygroup; and six R⁸ may be the same or different.

In the above formula (B)-1, the alkyl group and alkoxy group representedby R⁷ are the same as defined above.

In the above formula (B)-2, the alkyl group and alkoxy group representedby R⁸ are the same as defined above.

The repeating unit represented by the above formula (E) is, in view ofhole transport property, preferably a repeating unit represented by thefollowing formula (E)-1.

wherein R⁹ is an alkyl group, an aryl group, an arylalkyl group or anarylalkoxy group.

In the above formula (E)-1, the alkyl group, aryl group, arylalkyl groupand arylalkoxy group represented by R⁷ are the same as defined above.

When the compound of the present invention is a polymer compound, inview of charge transport property of the polymer compound, the compoundof the present invention may have, in addition to the repeating unitrepresented by the above formula (I), one or more of the repeating unitsrepresented by the following formulas (G), (H), (J) and (K).

wherein R¹⁰ represents an alkyl group, an aryl group, an arylalkyl groupor an arylalkoxy group; and two R¹⁰ may be the same or different.

wherein R¹¹ represents an alkyl group, an alkoxy group, an aryl group,an arylalkyl group or an arylalkoxy group; q represents an integerselected from 0 to 4; and a plurality of R¹¹ may be the same ordifferent.

wherein R¹² represents an alkyl group, an alkoxy group, an aryl group,an arylalkyl group or an arylalkoxy group; Z represents an oxygen atomor a sulfur atom; r is an integer of 0 to 3; and a plurality of R¹² maybe the same or different.

wherein R¹³ represents an alkyl group, an alkoxy group, an aryl group,an arylalkyl group or an arylalkoxy group; s is an integer of 0 to 2;and a plurality of R¹³ may be the same or different.

In the above formula (G), the alkyl group, aryl group, arylalkyl groupand arylalkoxy group represented by R¹⁰ are the same as defined above.

In the above formula (H), the alkyl group, alkoxy group, aryl group,arylalkyl group and arylalkoxy group represented by R¹¹ are the same asdefined above.

In the above formula (J), the alkyl group, alkoxy group, aryl group,arylalkyl group and arylalkoxy group represented by R¹² are the same asdefined above.

In the above formula (K), the alkyl group, alkoxy group, aryl group,arylalkyl group and arylalkoxy group represented by R¹³ are the same asdefined above.

When the compound of the present invention is a polymer compound, inview of luminous efficiency of the resultant compound preferably has arepeating unit represented by the above formula (I), the repeating unitrepresented by the above formula (C) and the repeating units representedby the above formulas (D) and (E).

Furthermore, when the compound of the present invention is a polymercompound, in view of harden ability, the compound of the presentinvention preferably has a repeating unit represented by the aboveformulas (D) and (E).

When the compound of the present invention is a polymer compound, in thecompound of the present invention, the uppermost ratio (molar ratio) ofthe repeating unit represented by the above formula (I) is usually, inview of stability of the compound, 1 relative to the total repeatingunits, preferably 0.5, more preferably 0.3, and most preferably 0.15.The lowermost ratio (molar ratio) is, in view of harden ability of thecompound, usually 0.01, preferably 0.02, more preferably 0.05 and mostpreferably 0.10.

Furthermore, when the compound of the present invention is a polymercompound having the repeating unit represented by the above formula (I),the repeating unit represented by the above formula (C) and therepeating units represented by the above formulas (D) and (E), the molarratio of the repeating unit represented by the above formula (C) isusually, 0.1 to 0.95 relative to the total repeating units andpreferably 0.3 to 0.9, whereas the whole molar ratio of the repeatingunits represented by the above formulas (D) and (E) is usually 0.01 to0.5 and preferably 0.05 to 0.3.

When the compound of the present invention is a polymer compound, thecompound of the present invention, in view of the life property of thelight-emitting device that is formed by using the compound, preferablyhas a polystyrene-equivalent number average molecular weight of 1×10³ to1×10⁸, more preferably 1×10³ to 1×10⁷, further preferably 1×10⁴ to 1×10⁷and particularly preferably 5×10⁴ to 1×10⁷.

When the compound of the present invention is a polymer compound, thecompound of the present invention, in view of harden ability, preferablyhas a polystyrene-equivalent weight average molecular weight of 1×10³ to1×10⁸, more preferably 1×10⁴ to 1×10⁷ and particularly preferably 1×10⁵to 1×10⁷.

In the specification, a number average molecular weight and a weightaverage molecular weight were obtained by size exclusion chromatography(SEC) (trade name: LC-10Avp manufactured by Shimadzu Corporation) as apolystyrene-equivalent number average molecular weight and weightaverage molecular weight. Of the methods of SEC, chromatography using anorganic solvent as a mobile phase is referred to as gel permeationchromatography (GPC). The polymer to be measured was dissolved intetrahydrofuran at a concentration of about 0.5 wt % and 30 μL of thesolution was loaded in GPC. As the mobile phase of GPC, tetrahydrofuranwas used and allowed to flow at a rate of 0.6 mL/minute. As the column,two TSKgel SuperHM-H (manufactured by Tosoh Corporation) columns and asingle TSKgel SuperH2000 (manufactured by Tosoh Corporation) column wereconnected in series. As the detector, a differential refractive indexdetector (trade name: RID-10A, manufactured by Shimadzu Corporation) wasused. Measurement was performed at 40° C.

Furthermore, when the compound of the present invention is a polymercompound, the compound of the present invention may be any one of analternating copolymer, a random copolymer, a block copolymer and a graftcopolymer, or may be a polymer compound having an intermediate structureof them, for example, a random copolymer partially having a blockcopolymer. The compound of the present invention is, in view offluorescence or phosphorescence quantum yield, preferably a randomcopolymer partially having a block copolymer, a block copolymer and agraft copolymer rather than a complete random copolymer. In the compoundof the present invention, a dendrimer having a branch in the main chainand three or more terminal portions is included.

When the compound of the present invention is a polymer compound, if apolymerizable group remains as it is as a terminal group of the compoundof the present invention, the luminescence property and life of thelight-emitting device produced by using the compound may sometimesdecrease. Because of this, the terminal group may be protected with astable group. As the terminal group, a group having a conjugated bondcontinued to a conjugated structure of the main chain is preferable. Forexample, a group connected to an aryl group or a monovalent heterocyclicgroup via a carbon-carbon bond is mentioned. Alternatively, asubstituent and the like described in JP 9-45478 A, Formula 10, may bementioned.

As the compound of the present invention, polymer compounds representedby the following formulas are mentioned. Note that v, w, x, y, z in theformulas represent composition ratios (molar ratios) of individualrepeating units.

As the compound of the present invention, low molecular compoundsrepresented by the following formulas are mentioned.

Next, a method for producing the compound of the present invention willbe described, taking the case where the compound of the presentinvention is a polymer compound as an example.

The compound may be manufactured in any method, for example, bycondensation polymerization of a compound represented by the formula:Z¹-A¹-Z². Note that in the above formula, A¹ represents a repeating unitrepresented by the above formula (I). Furthermore, in the above formula,Z¹ and Z² each independently represent a polymerizable group.

Furthermore, when the compound of the present invention is a polymercompound having a repeating unit represented by the above formula (A) to(H), (J) or (K), the compound of the present invention can be producedby condensation polymerization of a compound represented by the formula:Z³-A²-Z⁴ corresponding to the repeating unit. Furthermore, in the aboveformula, Z³ and Z⁴ each independently represent a polymerizable group.

Examples of the polymerizable group include a halogen atom, analkylsulfonate group, an arylsulfonate group, an arylalkylsulfonategroup, a boric acid ester residue, a sulfoniummethyl group, aphosphoniummethyl group, a phosphonatemethyl group, a monohalogenatedmethyl group, a boric acid residue (—B(OH)₂), a formyl group, a cyanogroup and a vinyl group.

Examples of the halogen atom serving as a polymerizable group include afluorine atom, a chlorine atom, a bromine atom and an iodine atom.

Examples of the alkylsulfonate group serving as a polymerizable groupinclude a methanesulfonate group, an ethanesulfonate group and atrifluoromethanesulfonate group.

Examples of the arylsulfonate group serving as a polymerizable groupinclude a benzenesulfonate group and a p-toluenesulfonate group.

Examples of the arylalkylsulfonate group serving as a polymerizablegroup include a benzylsulfonate group.

Examples of the boric acid ester residue serving as a polymerizablegroup include groups represented by the following formulas:

wherein Me represents a methyl group and Et represents an ethyl group.

Examples of the sulfoniummethyl group serving as a polymerizable groupinclude groups represented by the following formulas:

—CH₂S⁺Me₂X′⁻, —CH₂S⁺Ph₂X′⁻

wherein X′ represents a halogen atom and Ph represents a phenyl group.

Examples of the phosphoniummethyl group serving as a polymerizable groupinclude groups represented by the following formula:

—CH₂P⁺Ph₃X′⁻

wherein X′ represents a halogen atom.

Examples of the phosphonatemethyl group serving as a polymerizable groupinclude groups represented by the following formula:

—CH₂PO(OR′)₂

wherein R′ represents an alkyl group, an aryl group or an arylalkylgroup.

Examples of the monohalogenated methyl group serving as a polymerizablegroup include a methyl fluoride group, a methyl chloride group, a methylbromide group and a methyl iodide group.

When a zero-valence nickel complex for the Yamamoto coupling reaction orthe like is used, examples of the polymerizable group include a halogenatom, an alkylsulfonate group, an arylsulfonate group and anarylalkylsulfonate group. When a nickel catalyst or a palladium catalystfor the Suzuki coupling reaction or the like is used, examples thereofinclude an alkylsulfonate group, a halogen atom, a boric acid esterresidue and boric acid residue.

When the compound of the present invention is a polymer compound, thecompound of the present invention is produced by using a compound havinga plurality of polymerizable groups serving as a monomer, if necessary,dissolved in an organic solvent, and using, for example, an alkali andan appropriate catalyst and at a temperature of not less than themelting point of the organic solvent and not more than the boilingpoint. Examples of the method that can be used include methods describedin “Organic Reactions”, Vol. 14, pages 270-490, John Wiley & Sons, Inc.,1965, “Organic Syntheses”, Collective Volume VI, pages 407-411, JohnWiley & Sons, Inc., 1988, Chem. Rev., Vol. 95, page 2457 (1995), J.Organomet. Chem., Vol. 576, page 147 (1999), Makromol. Chem., Macromol.Symp.), Vol. 12, page 229 (1987).

When the compound of the present invention is a polymer compound, in themethod for producing the compound of the present invention, a knowncondensation reaction can be used depending upon the type ofpolymerizable group. Examples thereof include a method of polymerizingthe corresponding monomer by the Suzuki coupling reaction, a method ofpolymerizing by the Grignard reaction, a method of polymerizing by anNi(0) complex, a method of polymerizing by an oxidizing agent such asFeCl₃, a method of performing oxidative polymerization in anelectrochemical manner and a method by decomposing an intermediatepolymer having an appropriate leaving group.

Of these, a method of polymerizing by the Suzuki coupling reaction, amethod of polymerizing by the Grignard reaction, and a method ofpolymerizing by a nickel zero-valence complex are preferable in view ofstructural control.

Of the methods for producing the compound of the present invention, aproduction method using a polymerizable group selected from a halogenatom, an alkylsulfonate group, an arylsulfonate group and anarylalkylsulfonate group through and performed by a condensationpolymerization in the presence of a nickel zero-valence complex ispreferable.

Examples of a compound serving as a raw material for the compound of thepresent invention include a dihalogenated compound, abis(alkylsulfonate) compound, a bis(arylsulfonate) compound, abis(arylalkyl sulfonate) compound, a halogen-alkylsulfonate compound, ahalogen-arylsulfonate compound, a halogen-arylalkylsulfonate compound,an alkylsulfonate-arylsulfonate compound, analkylsulfonate-arylalkylsulfonate compound and anarylsulfonate-arylalkylsulfonate compound. Furthermore, when a polymercompound controlled in sequence is produced, examples of the compoundthat may be preferably used include a halogen-alkylsulfonate compound, ahalogen-arylsulfonate compound, a halogen-arylalkylsulfonate compound,an alkylsulfonate-arylsulfonate compound, analkylsulfonate-arylalkylsulfonate compound and anarylsulfonate-arylalkylsulfonate compound.

When the compound of the present invention is a polymer compound, amethod for producing the compound of the present invention is, in viewof easiness of synthesizing the polymer compound, preferably aproduction method using a polymerizable group, which is selected from ahalogen atom, an alkylsulfonate group, an arylsulfonate group, anarylalkylsulfonate group, a boric acid residue and a boric acid esterresidue such that the ratio of the total mole number (J) of the halogenatom, alkylsulfonate group, arylsulfonate group and arylalkylsulfonategroup contained in the whole raw-material compound and the total molenumber (K) of boric acid residue and boric acid ester residue becomessubstantially 1 (usually, K/J is 0.7 to 1.2), and performed by acondensation polymerization method using a nickel catalyst or apalladium catalyst.

Examples of a combination of compounds serving as raw materials (morespecifically, a compound represented by the above formula: Y¹-A¹-Y² anda compound represented by the above formula: Y³-A²-Y⁴) include acombination of a dihalogenated compound, a bis(alkylsulfonate) compound,a bis(arylsulfonate) compound or a bis(arylalkylsulfonate) compound anda diboric acid compound or diboric acid ester compound.

Furthermore, when a polymer compound controlled in sequence is produced,examples of the compound that may be preferably used include ahalogen-boric acid compound, a halogen-boric acid ester compound, analkylsulfonate-boric acid compound, an alkylsulfonate-boric acid estercompound, an arylsulfonate-boric acid compound, an arylsulfonate-boricacid ester compound, an arylalkylsulfonate-boric acid compound, anarylalkylsulfonate-boric acid compound and an arylalkylsulfonate-boricacid ester compound.

The organic solvent to be used in the condensation polymerization ispreferably treated in advance sufficiently in a deoxidization processand a dehydration process in order to suppress a side reaction. However,this is not applied to the case where a reaction is performed in atwo-phase system with water like the Suzuki coupling reaction.

Examples of the organic solvent to be used in the condensationpolymerization include saturated hydrocarbons such as pentane, hexane,heptane, octane, cyclohexane; unsaturated hydrocarbons such as benzene,toluene, ethylbenzene and xylene; halogenated saturated hydrocarbonssuch as carbon tetrachloride, chloroform, dichloromethane, chlorobutane,bromobutane, chloropentane, bromopentane, chlorohexane, bromohexane,chlorocyclohexane and bromocyclohexane; halogenated unsaturatedhydrocarbon such as chlorobenzene, dichlorobenzene and trichlorobenzene;alcohols such as methanol, ethanol, propanol, isopropanol, butanol andt-butyl alcohol; carboxylic acids such as formic acid, acetic acid andpropionic acid; ethers such as dimethyl ether, diethyl ether,methyl-t-butyl ether, tetrahydrofuran, tetrahydropyrane and dioxane;amines such as trimethylamine, triethylamine,N,N,N′,N′-tetramethylethylenediamine and pyridine; and amides such asN,N-dimethylformamide, N,N-dimethylacetamide, N,N-diethylacetamide andN-methylmorpholineoxide. Ethers are preferable and tetrahydrofuran anddiethylether are particularly preferable. These organic solvents may beused alone or in combination with two or more types.

In the condensation polymerization, an alkali and a suitable catalystmay be appropriately added to facilitate the reaction. The alkali andcatalyst are preferably dissolved sufficiently in the solvent to be usedin the reaction. To add the alkali or catalyst, a solution of the alkalior catalyst is added slowly while a reaction solution is stirred underthe atmosphere of an inert gas such as argon and nitrogen, orconversely, a reaction solution may be slowly added to a solution of thealkali or catalyst.

When the compound of the present invention is used for producing alight-emitting device, the purity of the compound influences performanceof the light-emitting device such as a luminescence property. Therefore,a raw material compound before subjected to polymerization is preferablypurified by a method such as distillation, sublimation orrecrystallization and thereafter subjected to polymerization. Furtherafter the polymerization, purification such as purification byreprecipitation and fractionation by chromatography is preferablyapplied.

When the compound of the present invention is produced, a compoundrepresented by the above formula (X) is preferably used.

In the above formula (X), an arylene group, a divalent heterocyclicgroup and a divalent aromatic amine group represented by Ar¹, aphenylene group represented by J¹, an alkylene group represented by J²,and a halogen atom represented by X¹ and X² are the same as definedabove.

As the halogen atom represented by X¹ and X², in view of easiness ofsynthesizing the compound to be obtained, a bromine atom and an iodineatom are preferable and a bromine atom is more preferable.

As the compound represented by the above formula (X), the compoundsrepresented by the following formulas are mentioned.

Furthermore, the compound represented by the above formula (X) may beproduced by any method. For example, the compound can be produced by amethod including reacting a compound represented by the above formula(XI) and a compound represented by the above formula (XII) in a base.

As the base to be used in the above reaction, an inorganic base such aspotassium carbonate, sodium carbonate, potassium hydroxide, and sodiumhydroxide or an organic base such as triethylamine is added in an amountof 1 equivalent or more relative to the above formula (XI) andpreferably 1 to 20 equivalents and subjected to the reaction.

In the above reaction, usually, a solvent is used. Examples of thesolvent include N,N-dimethylformamide, dimethylsulfoxide, toluene,dimethoxyethane and tetrahydrofuran.

The reaction temperature of the above reaction is usually 0° C. to theboiling point of the solvent and preferably 50 to 150° C. Furthermore,the reaction time of the above reaction is 0.5 to 100 hours.

<Composition>

The composition of the present invention is a composition comprising thecompound of the present invention. For example, a composition comprisingat least one selected from the group consisting of a hole transportmaterial, an electron transport material and a light-emitting material,and a polymer compound as mentioned above, is mentioned.

Furthermore, the composition of the present invention can be renderedalso to be a liquid composition further by adding a solvent thereto.More specifically, the liquid composition of the present invention is aliquid composition containing a polymer compound as mentioned above anda solvent. Hereinafter, the composition of the present invention and theliquid composition of the present invention are collectively referred toas “the liquid composition”.

The liquid composition of the present invention is useful for producinga light-emitting device such as a light-emitting device and an organictransistor. In the specification, “the liquid composition” refers to acomposition which is present as a liquid state when a device isproduced, and typically refers to a composition present in a liquidstate at normal pressure (more specifically, 1 atm) and at 25° C.Furthermore, the liquid composition is sometimes generally called asink, an ink composition and solution, etc.

The liquid composition of the present invention may contain, other thana polymer compound as mentioned above, a low molecular light-emittingmaterial, a hole transport material, an electron transport material, astabilizer, additives for controlling viscosity and/or surface tensionand an antioxidant, etc. These optional components each may be usedalone or in combination with two or more types.

Examples of the low molecular light-emitting material include anaphthalene derivative, anthracene, an anthracene derivative, perylene,a perylene derivative, a polymethine-based pigment, a xanthene-basedpigment, a coumarin-based pigment, a cyanine-based pigment, a metalcomplex containing a metal complex of an 8-hydroxyquinoline as a ligand,a metal complex containing a metal complex of an 8-hydroxyquinolinederivative as a ligand, other fluorescent metal complexes, an aromaticamine, tetraphenylcyclopentadiene, a tetraphenylcyclopentadienederivative, tetraphenylcyclobutadiene, a tetraphenylcyclobutadienederivative, fluorescent materials such as stilbene-, asilicon-containing aromatic-, oxazole-, furoxan-, thiazole-,tetraarylmethane-, thiadiazole-, pyrazole-, metacyclophane- andacetylene-based low molecular compounds. In addition, materialsdescribed in JP 57-51781 A and JP 59-194393 A etc. are included.

Examples of the hole transport material include polyvinyl carbazole anda derivative thereof, polysilane and a derivative thereof, apolysiloxane derivative having an aromatic amine in the side chain ormain chain, a pyrazoline derivative, an arylamine derivative, a stilbenederivative, a triphenyldiamine derivative, polyaniline and a derivativethereof, polythiophene and a derivative thereof, polypyrrole and aderivative thereof, poly(p-phenylenevinylene) and a derivative thereof,and poly(2,5-thienylenevinylene) and a derivative thereof.

Examples of the electron transport material include, an oxadiazolederivative, anthraquinodimethane and a derivative thereof, benzoquinoneand a derivative thereof, naphthoquinone and a derivative thereof,anthraquinone and a derivative thereof, tetracyanoanthraquinodimethaneand a derivative thereof, a fluorenone derivative,diphenyldicyanoethylene and a derivative thereof, a diphenoquinonederivative, metal complexes of 8-hydroxyquinoline and a derivativethereof; polyquinoline and a derivative thereof, polyquinoxaline and aderivative thereof, and polyfluorene and a derivative thereof.

Examples of the stabilizer include a phenolic antioxidant and aphosphoric antioxidant.

As additives for controlling viscosity and/or surface tension, a highmolecular-weight compound (thickening agent) and a poor solvent forincreasing viscosity, a low molecular-weight compound for decreasingviscosity and a surfactant for decreasing surface tension etc. may beused in appropriate combination.

As the high molecular-weight compound, any high molecular-weightcompound may be used as long as it does not inhibit light emission andcharge transport, and it is usually a soluble compound in the solventfor a liquid composition. As the high molecular-weight compound, a highmolecular weight polystyrene and a high molecular weightpolymethylmethacrylate, etc. can be used. The polystyrene-equivalentweight average molecular weight of the high molecular-weight compound ispreferably 500,000 or more and more preferably 1,000,000 or more.Furthermore, a poor solvent can be used as a thickening agent.

As the antioxidant, any antioxidant may be used as long as it does notinhibit light emission and charge transport, and if a compositioncontains a solvent, the antioxidant soluble in the solvent is usuallyused. Examples of the antioxidant include a phenolic antioxidant and aphosphoric antioxidant. Storage stability of the polymer compound andthe solvent can be improved by use of the antioxidant.

When the liquid composition of the present invention contains a holetransport material, the ratio of the hole transport material in theliquid composition is usually 1 to 80 wt % and preferably 5 to 60 wt %.Furthermore, when the liquid composition of the present inventioncontains an electron transport material, the ratio of the electrontransport material in the liquid composition is usually 1 to 80 wt % andpreferably 5 to 60 wt %.

When a film is formed by using the liquid composition in producing alight-emitting device, after the liquid composition is applied, all thatshould be done is just removing a solvent by drying. In addition, when acharge transport material and a light-emitting material are added, thesame procedure can be applied. Therefore, the liquid composition isextremely favorable in view of production. Note that drying may beperformed in a warm state of about 50 to 150° C. or under reducedpressure of about 10⁻³ Pa.

In forming a film using the liquid composition, a coating method can beused such as a spin coating method, a casting method, a microgravurecoating method, a gravure coating method, a bar coating method, a rollcoating method, a wire bar coating method, a dip coating method, a slitcoating method, a cap coating method, a capillary coating method, aspray coating method, a screen printing method, a flexo printing method,an offset printing method, an inkjet printing method and a nozzlecoating method.

The ratio of a solvent in the liquid composition is usually 1 to 99.9 wt% relative to the total weight of the liquid composition, preferably 60to 99.9 wt % and more preferably, 90 to 99.8 wt %. The viscosity of theliquid composition, which varies depending upon the printing method, ispreferably 0.5 to 500 mPa·s at 25° C. In the case where the liquidcomposition passes through an ejection apparatus as in the case ofinkjet printing method etc., viscosity is preferably 0.5 to 20 mPa·s at25° C. to prevent clogging during ejection and bending of sprayed liquidcomposition.

As the solvent contained in the liquid composition, a solvent capable ofdissolving or dispersing components of the liquid composition except thesolvent is preferable. Examples of the solvent include chlorine solventssuch as chloroform, methylene chloride, 1,2-dichloroethane,1,1,2-trichloroethane, chlorobenzene and o-dichloro benzene; ethersolvents such as tetrahydrofuran and dioxane; aromatic hydrocarbonsolvents such as toluene, xylene, trimethylbenzene and mesitylene;aliphatic hydrocarbon solvents such as cyclohexane, methylcyclohexane,n-pentane, n-hexane, n-heptane, n-octane, n-nonane and n-decane; ketonesolvents such as acetone, methylethylketone and cyclohexanone; estersolvents such as ethyl acetate, butyl acetate, methyl benzoate and ethylcellosolve acetate; polyhydric alcohols and a derivative thereof such asethylene glycol, ethylene glycol monobutyl ether, ethylene glycolmonoethylether, ethylene glycol monomethylether, dimethoxyethane,propylene glycol, diethoxymethane, triethylene glycol monoethylether,glycerin and 1,2-hexanediol; alcohol solvents such as methanol, ethanol,propanol, isopropanol and cyclohexanole; sulfoxide solvents such asdimethylsulfoxide; and amide solvents such as N-methyl-2-pyrrolidone andN,N-dimethylformamide. Furthermore, these solvents may be used alone orin combination of more than one types. Of the solvents, one or moreorganic solvents having a structure having at least one benzene ring andhaving a melting point of 0° C. or less and a boiling point of 100° C.or more is preferably contained in view of viscosity and film formingproperty etc. As the type of solvent, in view of solubility of thecomponents of the liquid composition except the solvent in an organicsolvent, uniformity of the film formed and viscosity property, etc., anaromatic hydrocarbon solvent, an aliphatic hydrocarbon solvent, an estersolvent and a ketone solvent are preferable. Preferable examples thereofinclude toluene, xylene, ethylbenzene, diethylbenzene, trimethylbenzene,mesitylene, n-propylbenzene, isopropylbenzene, n-butylbenzene,isobutylbenzene, s-butylbenzene, anisole, ethoxybenzene,1-methylnaphthalene, cyclohexane, cyclohexanone, cyclohexyl benzene,bicyclohexyl, cyclohexenylcyclohexanone, n-heptylcyclohexane,n-hexylcyclohexane, methylbenzoate, 2-propylcyclohexanone, 2-heptanone,3-heptanone, 4-heptanone, 2-octanone, 2-nonanone, 2-decanone anddicyclohexyl ketone. More preferably, at least one of the solventsincluding xylene, anisole, mesitylene, cyclohexylbenzene andbicyclohexylmethylbenzoate, is contained.

The number of types of solvents contained in the liquid composition, inview of film forming property and device characteristic, is preferably 2or more, more preferably 2 to 3 and particularly preferably 2.

When 2 types of solvents are contained in the liquid composition, one ofthe solvents may be in a solid state at 25° C. In view of film formingproperty, it is preferable that one of the solvents has a boiling pointof 180° C. or more and the other solvent has a boiling point of lessthan 180° C. It is more preferable that one of the solvents has aboiling point of 200° C. or more and the other solvent has a boilingpoint of less than 180° C. Furthermore, in view of viscosity, 0.2 wt %or more of the components of the liquid composition from which a solventis removed is preferably dissolved in the solvent at 60° C. In one ofthe two types of solvents, 0.2 wt % or more of the components of theliquid composition from which a solvent is removed is preferablydissolved at 25° C.

When three types of solvents are contained in the liquid composition,one to two types of solvents may be in a state of solid at 25° C. Inview of film forming property, it is preferable that at least one of thethree types of solvents has a boiling point of 180° C. or more and atleast one of the solvents has a boiling point of less than 180° C. It ismore preferable that at least one of the three types of solvents has aboiling point of 200° C. or more and 300° C. or less and at least one ofthe solvents has a boiling point of less than 180° C. In view ofviscosity, in two types of the three types of solvents, 0.2 wt % or moreof the components of the liquid composition from which a solvent isremoved is preferably dissolved at 60° C. In one of the three types ofsolvents, 0.2 wt % or more of the components of the liquid compositionfrom which a solvent is removed is preferably dissolved at 25° C.

When two or more types of solvents are contained in the liquidcomposition, in view of viscosity and film forming property, the contentof the solvent having the highest boiling point is preferably 40 to 90wt % of the total solvents contained in the liquid composition and morepreferably 50 to 90 wt % and further preferably 65 to 85 wt %.

<Film>

A film of the present invention will be described. The film is formed ofa polymer compound as mentioned above. As the type of film, a luminousfilm, a conductive film and an organic semiconductor film, etc. arementioned.

Furthermore, a film according to a second aspect of the presentinvention is formed by crosslinking of the polymer compound. The film isusually hardened by crosslinking caused by an external stimulus such asheat or light.

The heat for hardening a film is not particularly limited; however, itgenerally falls within the range of room temperature to 300° C. Theupper limit thereof is, in view of easiness of forming a film,preferably 250° C., further preferably 190° C. and most preferably 170°C. Furthermore, the lower limit is, in view of stability of a film atroom temperature, preferably 50° C., further preferably 70° C. and mostpreferably 100° C.

The light for hardening a film is not particularly limited; however,generally UV light, near ultra violet light and visible light are used,and UV light and near ultra violet light are preferable.

When the film of the present invention is hardened, the hardening ratecan be controlled depending upon the temperature, time or light exposurewavelength and exposure time.

The luminous film, in view of brightness of a device and emissionvoltage etc., preferably has, an emission quantum yield of 50% or more,more preferably 60% or more and further preferably 70% or more.

A conductive film preferably has a surface resistance of 1 KΩ/□ or less.The electric conductivity of the film can be improved by doping a Lewisacid and an ionic compound, etc. thereto. The surface resistance is morepreferably 100Ω/□ or less and further preferably, 10Ω/□ or less.

In an organic semiconductor film, a larger one of an electron mobilityand a hole mobility is preferably 10⁻⁵ cm²/V/second or more, morepreferably 10⁻³ cm²/V/second or more and further preferably 10⁻¹cm²/V/second or more. Furthermore, an organic transistor can be producedby using an organic semiconductor film. Specifically, an organictransistor can be obtained by forming an organic semiconductor film onan Si substrate having an insulating film such as SiO₂ and a gateelectrode formed thereon, and forming a source electrode and a drainelectrode of Au, etc.

<Organic Transistor>

The organic transistor of the present invention is an organic transistorcontaining a compound as mentioned above. Hereinafter, an embodiment ofthe organic transistor, that is, a field effect transistor, will bedescribed.

The compound of the present invention can be suitably used as a materialfor field effect transistor, in particular, as a material for an activelayer. As the structure of the field effect transistor, it is usuallysatisfactory if a source electrode and a drain electrode are provided incontact with an active layer formed of the compound of the presentinvention and a gate electrode is provided so as to sandwich aninsulating layer in contact with the active layer.

The field effect transistor is usually formed on a supporting substrate.As the supporting substrate, a glass substrate, a flexible filmsubstrate as well as a plastic substrate can be used.

A field effect transistor can be produced by a known method, forexample, a method described in JP 5-110069 A.

When an active layer is formed, use of a compound soluble in an organicsolvent is favorable and preferable in view of production. In forming afilm from a solution prepared by dissolving a compound soluble in anorganic solvent in a solvent, a spin coating method, a casting method, amicrogravure coating method, a gravure coating method, a bar coatingmethod, a roll coating method, a wire bar coating method, a dip coatingmethod, a slit coating method, a cap coating method, a capillary coatingmethod, a spray coating method, a screen printing method, a flexoprinting method, an offset printing method, an inkjet printing methodand a nozzle coating method can be used.

After the field effect transistor is produced and preferablyencapsulated to form an encapsulated field effect transistor. By virtueof this, the field effect transistor can be blocked from the air andsuppressed from deterioration of characteristics thereof.

As the encapsulating method, e.g., a method of covering with a UV rays(UV) curable resin, a thermosetting resin and an inorganic SiONx film,etc. and a method of joining glass plates and films with a UV rays (UV)curable resin or a thermosetting resin are mentioned. To effectivelyblock a field effect transistor from the air, it is preferred to performsteps from production thereof to encapsulation without being exposed tothe air (for example, in a dry nitrogen atmosphere or in vacuum).

<Organic Photoelectric Transducer>

An organic photoelectric transducer of the present invention (forexample, solar battery) is an organic photoelectric transducercontaining the aforementioned compound.

The compound of the present invention can be preferably used as amaterial for an organic photoelectric transducer, in particular, as anorganic semiconductor layer of a Schottky barrier type device using theinterface between an organic semiconductor and a metal, and furthermore,as an organic semiconductor layer of a pn-heterojunction type deviceusing the interface between an organic semiconductor and an inorganicsemiconductor or the interface between organic semiconductors.

Furthermore, the compound of the present invention can be preferablyused as an electron donating compound and an electron receptor compoundin a bulk heterojunction device increased in donor/acceptor contactarea, furthermore, an organic photoelectric transducer using apolymer/low molecular complex system, for example, as an electrondonating conjugated compound (diffusion support) of a bulkheterojunction organic photoelectric transducer having a fullerenederivative dispersed therein as an electron receptor.

As a structure of an organic photoelectric transducer, for example, in apn-heterojunction device, it is satisfactory if a p-type semiconductorlayer is formed on ITO, further an n-type semiconductor layer islaminated thereon, and an ohm electrode is provided thereon.

The organic photoelectric transducer is usually formed on a supportingsubstrate. As the supporting substrate, a glass substrate, a flexiblefilm substrate as well as a plastic substrate can be used.

An organic photoelectric transducer can be produced by a known method,for example, a method described in Synth. Met., 102, 982 (1999) and amethod described in Science, 270, 1789 (1995).

<Light-Emitting Device>

Next, a light-emitting device of the present invention will bedescribed.

The light-emitting device of the present invention is a light-emittingdevice having electrodes comprising an anode and a cathode, and anorganic layer provided between the electrodes and containing thecompound of the present invention, preferably a light-emitting devicehaving an organic layer serving as a light-emitting layer or a chargetransport layer. Examples of the light-emitting device of the presentinvention include (1) an light-emitting device having an electrontransport layer provided between a cathode and a light-emitting layer,(2) a light-emitting device having a hole transport layer providedbetween an anode and a light-emitting layer and (3) a light-emittingdevice having an electron transport layer provided between a cathode anda light-emitting layer and having a hole transport layer providedbetween an anode and the light-emitting layer.

More specifically, the following structures a) to d) are mentioned.

a) anode/light-emitting layer/cathode

b) anode/hole transport layer/light-emitting layer/cathode

c) anode/light-emitting layer/electron transport layer/cathode

d) anode/hole transport layer/light-emitting layer/electron transportlayer/cathode

(wherein symbol “/” indicates that individual layers are laminated inadjacent to each other. The same is applied in the following)

The light-emitting layer is a layer having a function of emitting light.The hole transport layer is a layer having a function of transportingholes, The electron transport layer is a layer having a function oftransporting electrons. Note that the electron transport layer and thehole transport layer are collectively called a charge transport layer.As the light-emitting layer, hole transport layer and electron transportlayer each may consists of two layers or more. Furthermore, the holetransport layer provided in adjacent to a light-emitting layer issometimes called as an interlayer.

As a method for forming a light-emitting layer, a method of forming afilm from a solution is mentioned. In forming a film from a solution, aspin coating method, a casting method, a microgravure coating method, agravure coating method, a bar coating method, a roll coating method, awire bar coating method, a dip coating method, a slit coating method, acap coating method, a capillary coating method, a spray coating method,a screen printing method, a flexo printing method, an offset printingmethod, an inkjet printing method and a nozzle coating method can beused. Note that the formation of a film from a solution is useful forforming films of a hole transport layer and an electron transport layer(described later).

When a film is formed from a solution by using the compound of thepresent invention in producing a light-emitting device, all that shouldbe done after the solution is applied, is just removing a solvent bydrying. Furthermore, even in the case where a charge transport materialand a light-emitting material are added, the same procedure can beapplied and thus favorable in production.

The film thickness of a light-emitting layer, which may be selected suchthat appropriate driving voltage and luminous efficiency values areobtained, is, for example, 1 nm to 1 μm, preferably 2 nm to 500 nm andfurther preferably 5 nm to 200 nm.

In the light-emitting device of the present invention, a light-emittingmaterial except the aforementioned compound may be used in combinationin a light-emitting layer. Furthermore, in the light-emitting device ofthe present invention, a light-emitting layer containing alight-emitting material except the aforementioned compound and alight-emitting layer containing the aforementioned compound may belaminated.

Examples of a light-emitting material except the aforementioned compoundinclude low molecular compounds such as a naphthalene derivative,anthracene and a derivative thereof, perylene and a derivative thereof,pigments including a polymethine-based pigment, a xanthene-basedpigment, a coumarin-based pigment and a cyanine-based pigment, a metalcomplex of 8-hydroxyquinoline and a derivative thereof, an aromaticamine, tetraphenylcyclopentadiene and a derivative thereof andtetraphenylbutadiene and a derivative thereof. In addition, thecompounds described in JP 57-51781 A and JP 59-194393 A, etc. may bementioned.

When the light-emitting device of the present invention has a holetransport layer, the hole transport material to be used herein is thesame as the hole transport material described in the section of theliquid composition; however, preferable examples thereof include polymerhole transport materials such as polyvinylcarbazole and a derivativethereof, polysilane and a derivative thereof, a polysiloxane derivativehaving an aromatic amine compound group in the side chain or main chain,polyaniline and a derivative thereof, polythiophene and a derivativethereof, poly(p-phenylenevinylene) and a derivative thereof,poly(2,5-thenylenevinylene) and a derivative thereof. More preferableexamples thereof include, polyvinyl carbazole and a derivative thereof,polysilane and a derivative thereof and a polysiloxane derivative havingan aromatic amine in the side chain or main chain. In the case of a lowmolecular hole transport material, it is preferably dispersed in apolymer binder and put in use.

As a method for forming a hole transport layer, in the case of a lowmolecular hole transport material, a method for forming a film from asolution containing a polymer binder mixed therein is mentioned.Furthermore, in the case of a high-molecular hole transport material, amethod for forming a film from a solution is mentioned.

As the polymer binder to be mixed, a polymer binder that does notsignificantly inhibit charge transport is preferable and a polymerbinder that does not significantly absorb visible light is suitablyused. Examples of the polymer binder include polycarbonate,polyacrylate, polymethylacrylate, polymethylmethacrylate, polystyrene,polyvinyl chloride and polysiloxane.

The film thickness of the hole transport layer, which may be selectedsuch that appropriate driving voltage and luminous efficiency values areobtained, is for example, 1 nm to 1 μm, preferably 2 nm to 500 nm, andfurther preferably 5 nm to 200 nm.

When the light-emitting device of the present invention has an electrontransport layer, the electron transport material to be used is the sameas the electron transport material as described in the section of theliquid composition; however, preferable examples thereof include anoxadiazole derivative, benzoquinone and a derivative thereof,anthraquinone and a derivative thereof, a metal complex of 8-hydroxyquinoline and a derivative thereof, polyquinoline and a derivativethereof, polyquinoxaline and a derivative thereof and polyfluorene and aderivative thereof; and more preferable examples thereof include2-(4-biphenylyl)-5-(4-t-butylphenyl)-1,3,4-oxadiazole, benzoquinone,anthraquinone, tris(8-quinolinol)aluminum and polyquinoline.

As a method for forming a film of the electron transport layer method,in the case of a low-molecular electron transport material, a vapordeposition method for forming a film from a powder, and a method forforming a film from a solution or a molten state are mentioned; in thecase of a high-molecular electron transport material, a method forforming a film from a solution or a molten state is mentioned. When afilm is formed from a solution or a molten state, a polymer binder maybe used in combination.

As the polymer binder to be added, a polymer binder that does notsignificantly inhibit charge transport is preferable, and a polymerbinder that does not significantly absorb visible light is suitablyused. Examples of the polymer binder include poly(N-vinylcarbazole),polyaniline and a derivative thereof, polythiophene and a derivativethereof, poly(p-phenylenevinylene) and a derivative thereof,poly(2,5-thienylenevinylene) and a derivative thereof, polycarbonate,polyacrylate, polymethylacrylate, polymethylmethacrylate, polystyrene,polyvinyl chloride and polysiloxane.

The film thickness of the electron transport layer may be selected suchthat appropriate driving voltage and luminous efficiency values areobtained, for example, 1 nm to 1 μm, preferably 2 nm to 500 nm, andfurther preferably 5 nm to 200 nm.

Furthermore, of the charge transport layers provided in adjacent to anelectrode, a charge transport layer having a function of improving anefficiency of charge injection from an electrode and having an effect ofreducing the driving voltage of a device is sometimes particularlycalled a charge injection layer (hole injection layer, electroninjection layer).

Furthermore, to improve adhesion with an electrode and to improveinjection of charge from an electrode, the charge injection layer or aninsulating layer may be provided in adjacent to the electrode. Moreover,to improve adhesion at the interface and prevent contamination, etc., athin buffer layer may be inserted in the interface between a chargetransport layer and a light-emitting layer.

The order and number of layers to be laminated and the thickness of eachlayer may be appropriately selected in consideration of luminousefficiency and device life.

In the present invention, as a light-emitting device having a chargeinjection layer provided therein, a light-emitting device having acharge injection layer provided in adjacent to a cathode and alight-emitting device having a charge injection layer provided inadjacent to an anode are mentioned.

Specific examples thereof include the following structures e) to p).

e) anode/charge injection layer/light-emitting layer/cathode,

f) anode/light-emitting layer/charge injection layer/cathode,

g) anode/charge injection layer/light-emitting layer/charge injectionlayer/cathode,

h) anode/charge injection layer/hole transport layer/light-emittinglayer/cathode,

i) anode/hole transport layer/light-emitting layer/charge injectionlayer/cathode,

j) anode/charge injection layer/hole transport layer/light-emittinglayer/charge injection layer/cathode,

k) anode/charge injection layer/light-emitting layer/charge transportlayer/cathode,

l) anode/light-emitting layer/electron transport layer/charge injectionlayer/cathode,

m) anode/charge injection layer/light-emitting layer/electron transportlayer/charge injection layer/cathode,

n) anode/charge injection layer/hole transport layer/light-emittinglayer/charge transport layer/cathode,

o) anode/hole transport layer/light-emitting layer/electron transportlayer/charge injection layer/cathode,

p) anode/charge injection layer/hole transport layer/light-emittinglayer/electron transport layer/charge injection layer/cathode.

Examples of the charge injection layer include a layer containing aconductive polymer; a layer provided between an anode and a holetransport layer and containing a material having an intermediateionization potential value between an anode material and a holetransport material contained in the hole transport layer, and a layerprovided between a cathode and an electron transport layer andcontaining a material having an intermediate affinity value for electronbetween a cathode material and an electron transport material containedin the electron transport layer.

When the charge injection layer is a layer containing a conductivepolymer, the electric conductivity of the conductive polymer ispreferably 10⁻⁵ to 10³ S/cm. To reduce current leakage between emissionpixels, the electric conductivity is more preferably 10⁻⁵ to 10² S/cmand further preferably 10⁻⁵ to 10¹ S/cm. Usually, to control theelectric conductivity of the conductive polymer to be 10⁻⁵ to 10³ S/cm,an appropriately amount of ion is doped in the conductive polymer.

Type of ion to be doped is anion in the case of a hole injection layerand cation in the case of an electron injection layer. Examples of theanion include polystyrene sulfonate ion, alkyl benzene sulfonate ion andcamphor sulfonate ion. Examples of the cations include a lithium ion, asodium ion, a potassium ion and a tetrabutylammonium ion.

The film thickness of the charge injection layer is, for example, 1 nmto 100 nm and preferably 2 nm to 50 nm.

Examples of the material to be used for the charge injection layerinclude polyaniline and a derivative thereof, polythiophene and aderivative thereof, polypyrrole and a derivative thereof,polyphenylenevinylene and a derivative thereof, polythienylenevinyleneand a derivative thereof, polyquinoline and a derivative thereof,polyquinoxaline and a derivative thereof, a conductive polymer such as apolymer having an aromatic amine structure in the main chain or sidechain, metal phthalocyanine (copper phthalocyanine, etc.) and carbon.

The insulating layer is a layer having a function of facilitating chargeinjection. The average thickness of the insulating layer is, usually,0.1 to 20 nm, preferably 0.5 to 10 nm and more preferably 1 to 5 nm.Examples of a material for the insulating layer include a metalfluoride, a metal oxide and an organic insulating material. As alight-emitting device having an insulating layer provided therein, alight-emitting device having an insulating layer provided in adjacent toa cathode and a light-emitting device having an insulating layerprovided in adjacent to an anode are mentioned.

Specific examples thereof include the following structures q) to ab).

q) anode/insulating layer/light-emitting layer/cathode,

r) anode/light-emitting layer/insulating layer/cathode,

s) anode/insulating layer/light-emitting layer/insulating layer/cathode,

t) anode/insulating layer/hole transport layer/light-emittinglayer/cathode,

u) anode/hole transport layer/light-emitting layer/insulatinglayer/cathode,

v) anode/insulating layer/hole transport layer/light-emittinglayer/insulating layer/cathode,

w) anode/insulating layer/light-emitting layer/electron transportlayer/cathode,

x) anode/light-emitting layer/electron transport layer/insulatinglayer/cathode,

y) anode/insulating layer/light-emitting layer/electron transportlayer/insulating layer/cathode,

z) anode/insulating layer/hole transport layer/light-emittinglayer/electron transport layer/cathode,

aa) anode/hole transport layer/light-emitting layer/electron transportlayer/insulating layer/cathode,

ab) anode/insulating layer/hole transport layer/light-emittinglayer/electron transport layer/insulating layer/cathode.

As the substrate for forming the light-emitting device of the presentinvention, any substrate may be used as long as it remains unchangedwhen an electrode is formed and an organic material layer is formed.Examples of the substrates include glass, plastic, a polymer film andsilicon substrates. In the case of an opaque substrate, the oppositeelectrode is preferably transparent or semitransparent.

In the present invention, at least one of the electrodes comprising ananode and a cathode is usually transparent or semitransparent andpreferably the anode is transparent or semitransparent.

As a material for the anode, a conductive metal oxide film and asemitransparent metal film, etc. are used. More specifically, a film(NESA, etc.) formed of conductive glass using indium oxide, zinc oxide,tin oxide and a complex thereof, that is, indium/tin/oxide (ITO) andindium/zinc/oxide, etc. gold, platinum, silver and copper, etc. areused, and ITO, indium/zinc/oxide and tin oxide are preferable. Examplesof a forming method include a vapor deposition method, a sputteringmethod, an ion-plating method and a plating method. Furthermore, as theanode, a transparent conducting film of an organic substance such aspolyaniline and a derivative thereof and polythiophene and a derivativethereof.

The film thickness of the anode is, in view of lightpermeability/electric conductivity, for example, 10 nm to 10 μm,preferably 20 nm to 1 μm and further preferably 50 nm to 500 nm.

Furthermore, to facilitate charge injection, a layer formed of e.g., aphthalocyanine derivative, a conductive polymer or carbon, or a layerformed of e.g., a metal oxide, a metal fluoride or an organic insulatingmaterial may be provided on the anode.

As a material for the cathode, a material having a small work functionis preferable. Examples thereof that are used include a metal such aslithium, sodium, potassium, rubidium, cesium, beryllium, magnesium,calcium, strontium, barium, aluminum, scandium, vanadium, zinc, yttrium,indium, cerium, samarium, europium, terbium and ytterbium; an alloy oftwo or more types of them or an alloy of one or more of them with one ormore of, e.g., gold, silver, platinum, copper, manganese, titanium,cobalt, nickel, tungsten and tin; and graphite or an graphiteintercalation compound. Examples of the alloy include a magnesium-silveralloy, a magnesium-indium alloy, a magnesium-aluminum alloy, anindium-silver alloy, a lithium-aluminum alloy, a lithium-magnesiumalloy, a lithium-indium alloy and a calcium-aluminum alloy. The cathodemay have a laminate structure of 2 layers or more.

The film thickness of the cathode is, in view of electric conductivityand durability, for example, 10 nm to 10 μm, preferably 20 nm to 1 μm,and further preferably 50 nm to 500 nm.

As a method for forming the cathode, a vapor deposition method, asputtering method and a laminate method in which a metal film isattached by thermo compression bonding are used. Furthermore, betweenthe cathode and the organic material layer, a layer formed of aconductive polymer or a layer formed of a metal oxide, a metal fluoride,an organic insulating material or the like may be provided.Alternatively after the cathode is formed, a protecting layer forprotecting the light-emitting device may be attached. To use thelight-emitting device stably for a long time, a protecting layer and/ora protecting cover is preferably attached to protect the device from theoutside.

As the protecting layer, a resin, a metal oxide, a metal fluoride and ametal borate, etc. can be used. Furthermore, as the protecting cover, aglass plate, a plastic plate having a surface treated to lower waterpermeability, and the like can be used. A method in which the cover isallowed to adhere airtight to a device substrate with a thermosettingresin or a light curable resin can be preferably used. If a spacer isused to keep a space, the device is easily protected from damage. If aninert gas such as nitrogen and argon is supplied to the space, thecathode can be prevented from being oxidized. Furthermore, if adesiccating agent such as barium oxide is placed in the space, thedevice is easily prevented from damage with a moisture contentintroduced by adsorption in a production step. At least one of thesemeasures is preferably employed.

The light-emitting device of the present invention can be used indisplays such as a surface light source, a segment display, a dot matrixdisplay, a liquid crystal display (for example, a backlight) and a flatpanel feris play.

To obtain a planer emission by using the light-emitting device of thepresent invention, a planar anode and cathode are arranged so as tooverlap them. Furthermore, to obtain patterned emission of light, thereare a method of placing a mask having a patterned window in the surfaceof the surface light-emitting device, a method of forming an extremelythick organic material layer in a non light-emitting section such thatlight is not substantially emitted, and a method of forming a patternedelectrode as either one of an anode and cathode or both electrodes.Patterns are formed by any one of these methods and electrodes arearranged so as to independently turn ON/OFF. In this manner, asegment-type display device capable of displaying numeric characters andletters, and simple symbols, etc. can be obtained. Furthermore, toobtain a dot matrix device, an anode and a cathode are formed in theform of stripe and arranged so as to cross perpendicularly. A partialcolor display and multi-color display can be realized by a method ofdistinctively applying a plurality of types of light-emitting materialsdifferent in luminous color and a method of using a color filter or afluorescence conversion filter. A dot matrix device can be passivelydriven or may be actively driven in combination with TFT, etc. Thesedisplay devices can be used as displays for computers, televisions,mobile terminals, mobile phones, car-navigation and view finders ofvideo cameras, etc.

Furthermore, the surface light-emitting device is usually an autonomouslight-emitting thin device and can be preferably used as a surface lightsource for a backlight of a liquid crystal display or surfaceillumination light source. For example, as the illumination lightsource, light emission such as white light emission, red light emissionand green light emission or blue light emission are mentioned.Furthermore, if a flexible substrate is used, the light-emitting devicecan be used also as a curved-surface light source and a curved-surfacedisplay device.

EXAMPLES

Examples will be shown below to describe the present invention morespecifically; however, the present invention is not limited to these.

Synthesis Example 1 Synthesis of Compound M-1

Under an argon atmosphere, divinylcarbinol (25.24 g), triethylorthoacetate (340 g) and propionic acid (0.20 g) were blended and warmedto 130° C. for 4 hours while removing ethanol by use of Dean-Stark.After completion of the reaction, the resultant reaction solution wascooled. To the reaction solution, hexane (300 ml) and ion-exchangedwater (300 ml) were added, and stirred at 60° C. for 3 hours. Afterlayers were separated, an organic layer was washed with ion-exchangedwater (300 ml×3 times) and dried over sodium sulfate. The resultantorganic layer was concentrated by passing it through an alumina flushcolumn. To the resultant oil, again, hexane (300 ml), ion-exchangedwater (300 ml) and propionic acid (0.20 g) were added and stirred at 60°C. for 8 hours. After layers were separated, an organic layer was washedwith ion-exchanged water (300 ml×3 times) and dried over sodium sulfate.The resultant organic layer was concentrated by passing it through analumina flush column to obtain compound M-1 (28 g) represented by theabove formula M-1.

¹H-NMR (270 MHz, CDCl₃): δ=1.25 (t, 3H), 2.07 (q, 2H), 2.41 (m, 4H),5.05 (dd, 2H), 5.70 (m, 1H), 6.09 (dd, 1H), 6.29 (m, 1H) ppm.

Synthesis Example 2 Synthesis of Compound M-2

Under an argon atmosphere, compound M-1 (14.65 g) and diethyl ether (770ml) were blended and cooled to 0° C. Subsequently, to the resultantsolution mixture, a 1 M lithium aluminum hydride ether solution (50 ml)was added dropwise for one hour and stirred for one hour while thetemperature was kept at 0° C. To the resultant reaction solution, a 5 wt% aqueous sodium hydroxide solution (100 ml) was slowly added dropwiseand quenched. Thereafter, an organic layer was washed with water (100ml×3 times) and the organic layer was dried over sodium sulfate. Theresultant organic layer was concentrated by passing it through analumina flush column to obtain compound M-2 (8.0 g) represented by theabove formula M-2.

¹H-NMR (270 MHz, CDCl₃): δ=1.67 (tt, 2H), 2.13-2.28 (m, 3H), 3.63 (q,2H), 5.04 (dd, 2H), 5.72 (dd, 1H), 6.07 (dd, 1H), 6.30 (m, 1H) ppm.

Synthesis Example 3 Synthesis of Compound M-3

Under an argon atmosphere, compound M-2 (18.98 g) and dichloromethane(730 ml) were blended and cooled to 0° C. To the resultant solutionmixture, triethylamine (58 ml) was added dropwise and then methanesulfonylchloride (24 ml) was added dropwise and stirred for 2 hourswhile the temperature was kept at 0° C. To the resultant reactionsolution, water was added and quenched and thereafter, extraction withether and dehydration over sodium sulfate were performed to obtainyellow oil (32 g).

Under an argon atmosphere, the yellow oil (32 g), lithium bromide (36 g)and THF (400 ml) were blended and refluxed for 7 hours. The resultantreaction solution was cooled and ion-exchanged water (200 ml) andtoluene (500 ml) were added and then, layers were separated. The organiclayer was washed with ion-exchanged water (100 ml×5 times) and driedover sodium sulfate. The resultant organic layer was concentrated. Afterhexane (100 ml) was added, the organic layer was concentrated by passingit through an alumina flush column. The resultant oil was fractionated(3 mmHg, 27° C.) to obtain compound M-3 (15.1 g) represented by theabove formula M-3.

¹H-NMR (270 MHz, CDCl₃): δ=1.96 (tt, 2H), 2.22-2.29 (m, 2H), 3.41 (t,2H), 5.05 (dd, 2H), 5.65 (m, 1H), 6.10 (dd, 1H), 6.30 (m, 1H) ppm.

Example 1 Synthesis of Compound M-4

Under an argon atmosphere, in a 300 mL four-neck flask, compound M-3(5.29 g), 2,7-dibromofluorene (4.67 g) and DMSO (35 ml) were blended. Tothe resultant solution mixture, potassium hydroxide (3.43 g) andpotassium iodide (0.17 g) mashed in a mortar were added and warmed at85° C. for 45 minutes. To the resultant solution mixture, ion-exchangedwater (50 ml) and ethyl acetate (100 ml) were added and then layers wereseparated. The organic layer was washed with a saturated saline solution(100 ml×10 times), dried over sodium sulfate and then concentrated. Theresultant oil was purified by silica gel column chromatography(developing solvent: hexane) to obtain compound M-4 (4.9 g) representedby the above formula M-4 as a white solid substance.

¹H-NMR (270 MHz, CDCl₃): δ=0.68 (m, 4H), 1.81-1.96 (m, 8H), 4.99 (dd,4H), 5.44 (m, 2H), 5.89 (dd, 2H), 6.22 (td, 2H), 7.47 (m, 6H) ppm.

MS (APCI-MS: Positive) m/z: 512 ([M]⁺).

Example 2 Synthesis of Compound M-5

Under an argon atmosphere, in a 100 mL four-neck flask, compound M-3(1.88 g), 2,5-dibromohydroquinone (2.51 g) and ethanol (7 ml) wereblended. To the resultant solution mixture, potassium hydroxide (0.97 g)mashed in a mortar was added and warmed at 85° C. for 9 hours. Aftercompletion of the reaction, to the resultant reaction solution,ion-exchanged water (20 ml) and ethyl acetate (20 ml) were added andlayers were separated. Thereafter, the organic layer was washed withion-exchanged water (40 ml×3 times), dried over sodium sulfate and thenconcentrated. The resultant oil was purified by silica gel columnchromatography (developing solvent: toluene/hexane=1:1) to obtaincompound M-5 (1.3 g) represented by the above formula M-5 as a whitesolid substance.

¹H-NMR (270 MHz, CDCl₃): δ=1.87-1.96 (m, 4H), 2.28-2.35 (m, 4H), 3.94(t, 4H), 5.05 (dd, 4H), 5.75 (m, 2H), 6.10 (m, 2H), 6.31 (m, 2H), 7.08(s, 2H) ppm.

Example 3 Synthesis of Compound M-7

Under an argon atmosphere, in a 100 mL four-neck flask, compound M-3(1.63 g), compound M-6 (1.63 g) represented by the above formula M-6 andethanol (7 ml) were blended. To the resultant solution mixture,potassium hydroxide (0.97 g) mashed in a mortar was added and warmed at60° C. for 40 hours. After completion of the reaction, to the resultantreaction solution, ion-exchanged water (50 ml) and toluene (50 ml) wereadded. After layers were separated, an organic layer was washed withion-exchanged water (40 ml×3 times), dried over sodium sulfate and thenconcentrated. The resultant oil was purified by silica gel columnchromatography (developing solvent: toluene/hexane=1:1) to obtaincompound M-7 (1.1 g) represented by the above formula M-7 as a whitesolid substance.

Note that compound M-6 was synthesized with reference to EP1344788.

¹H-NMR (270 MHz, CDCl₃): δ=1.97-2.06 (m, 4H), 2.36-2.43 (m, 4H), 4.10(t, 4H), 5.04 (dd, 4H), 5.78 (m, 2H), 6.14 (m, 2H), 6.32 (m, 2H), 7.32(s, 2H), 7.73 (s, 2H) ppm.

Synthesis Example 4 Synthesis of Compound M-8

Under nitrogen gas atmosphere, to a mixture of 2,7-dibromofluorene (75g, 0.22 mol), hexylbenzene (334 ml) and trifluoromethanesulfonic acid(42 ml) stirred at room temperature, sodium 3-mercaptopropanesulfonate(8.1 g) was added and stirred at 45° C. for 9 hours. The resultantreaction solution was cooled to room temperature and then added tohexane (1 L). Excess hexyl benzene was distilled away by distillationunder reduced pressure (105.5° C., 20 hPa), diluted with hexane and thenadded to methanol. The precipitated 2,7-dibromofluorenone was removed byfiltration. The resultant filtrate was concentrated and then dilutedwith toluene, and isopropyl alcohol was added to precipitate a solidsubstance. The resultant solid substance was recrystallized fromtoluene/isopropyl alcohol to obtain compound M-8 (53 g) represented bythe above formula M-8 as a white solid substance.

¹H-NMR (270 MHz, CDCl₃): δ=0.88 (t, 3H), 1.20-1.45 (m, 6H), 1.54-1.62(m, 2H), 2.57 (t, 2H), 4.96 (s, 1H), 6.94 (d, 2H), 7.10 (d, 2H), 7.42(s, 2H), 7.48 (dd, 2H), 7.60 (d, 2H) ppm.

Example 4 Synthesis of Compound M-9

Under an argon atmosphere, in a 100 mL four-neck flask, compound M-3(0.96 g), compound M-8 (2.42 g) and dimethylsulfoxide (12 ml) wereblended. To the resultant solution mixture, potassium hydroxide (1.2 g)and potassium iodide (0.08 g) mashed in a mortar were added and stirredat room temperature for 5 hours. After completion of the reaction, tothe resultant reaction solution, ion-exchanged water (20 ml) and toluene(30 ml) were added. After layers were separated, an organic layer waswashed with a saturated saline solution (30 ml×10 times) and dried oversodium sulfate and then concentrated. The resultant oil was purified bysilica gel column chromatography (developing solvent:toluene/hexane=1:10) to obtain compound M-9 (2.0 g) represented by theabove formula M-9 as colorless oil.

¹H-NMR (270 MHz, CDCl₃): δ=0.75-0.87 (m, 5H), 1.20-1.39 (m, 6H),1.52-1.56 (m, 2H), 2.00-2.31 (m, 2H), 2.37-2.44 (m, 2H), 2.50-2.56 (t,2H), 4.92-5.10 (dd, 2H), 5.44-5.53 (td, 1H), 5.89-5.97 (dd, 1H),6.17-6.30 (td, 1H), 7.00-7.16 (m, 4H), 7.18-7.28 (dd, 2H), 7.47 (d, 2H),7.55 (d, 2H) ppm.

Example 5 Synthesis of Compound M-11

Under an argon atmosphere, in a 300 mL three-neck flask, compound M-10(5.1 g), compound M-3 (3.7 g) and dimethylsulfoxide (100 ml) wereblended. To this, potassium hydroxide (1.4 g) was added and stirred atroom temperature for 6 hours. After completion of the reaction, water(30 ml) was added. After layers were separated, the resultant organiclayer was washed with water, then dried over sodium sulfate, andconcentrated to dryness. Subsequently, purification was performed bycolumn chromatography using hexane: chloroform (=6:1) as a developingsolvent and silica gel as a filler. Recrystallization was performed toobtain compound M-11 represented by the above formula.

Note that compound M-10 was synthesized with reference to U.S. Pat. No.U.S. Pat. No. 5,447,960.

¹H-NMR (270 MHz, CDCl₃); 1.88 (m, 4H), 2.26 (q, 4H)), 3.93 (t, 4H),5.15-4.95 (m, 4H), 5.76-5.66 (m, 2H), 6.33-6.27 (m, 2H), 6.75 (d, 4H),7.03 (d, 4H), 7.57-7.43 (m, 6H).

Synthesis Example 5 Synthesis of Compound MM-1

Under an argon atmosphere, in a 500 ml four-neck flask,2,7-dibromofluorene (22.7 g), 5-bromo-1-octene (21.9 g), potassiumhydroxide (16.7 g), potassium iodide (1.2 g) and dimethylsulfoxide (170ml) were blended and warmed to 80° C. for 4 hours. After completion ofthe reaction, the resultant reaction solution was cooled to roomtemperature. To this, water (300 ml) and toluene (300 ml) were added andlayers were separated. Subsequently, the organic layer was washed 5times with a saturated aqueous sodium chloride solution (300 ml). Afterthe resultant organic layer was dried over sodium sulfate, purificationwas performed by column chromatography using hexane as a developingsolvent and silica gel as a filler to obtain compound MM-1 representedby the above formula MM-1.

ESI-MS: 460 [M]⁺

¹H-NMR (270 MHz, CDCl₃); δ=0.69 (t, 4H), 1.83 (m, 4H), 1.93 (m, 4H),4.85 (d, 4H), 5.56 (m, 2H), 7.44-7.53 (m, 6H).

Synthesis Example 6 Synthesis of Compound MM-3

Under an argon atmosphere, in a 300 ml three-neck flask,2,7-dibromofluorene (8.1 g), 8-bromo-1-octene (10.0 g), potassiumhydroxide (6.0 g), potassium iodide (0.42 g) and dimethylsulfoxide (60ml) were blended and warmed to 80° C. for 4 hours. After completion ofthe reaction, the reaction solution was cooled to room temperature. Tothis, water (100 ml) and toluene (100 ml) were blended. After layerswere separated, the resultant organic layer was washed 5 times with asaturated aqueous sodium chloride solution (100 ml). After the resultantorganic layer was dried over sodium sulfate, purification was performedby column chromatography using hexane as a developing solvent and silicagel as a filler to obtain compound MM-3 represented by the above formulaMM-3.

ESI-MS: 544 [M]⁺

¹H-NMR (270 MHz, CDCl₃); δ=0.58 (m, 4H), 1.06 (m, 8H), 1.18 (m, 4H),1.92 (m, 8H), 4.90 (d, 4H), 5.73 (m, 2H), 7.43-7.52 (m, 6H).

Synthesis Example 7 Synthesis of Compound MM-X

A 5 L-three-neck flask was purged with nitrogen.1-Bromo-3-n-hexylbenzene (226 g) was weighed and dissolved in a 2.5 Ldewatered THF. This solution was cooled to −75° C. or less and a 2.5 Mn-butyllithium/hexane solution (358 ml) was added dropwise and stirredfor 5 hours while the temperature was kept at −75° C. or less. To thissolution, a solution of 2-methoxycarbonyl-4,4′-dibromobiphenyl (150 g)dissolved in 400 ml of dewatered THF was added dropwise while thetemperature was kept at −70° C. or less. The solution was graduallyincreased to room temperature and then stirred overnight. While thereaction solution was stirred at 0° C., 150 ml of water was addeddropwise. After a solvent was distilled away, water (200 ml) was addedto the residue. Extraction was performed once with hexane (1 L) andtwice with hexane (100 ml). Organic layers were combined and washed witha saturated saline solution (200 ml). The water layer was re-extractedwith hexane (100 ml) and then, dried over magnesium sulfate. The solventwas distilled away to obtain a crude product (264 g) of compound MM-Xand used in the next step without purification.

Note that 2-methoxycarbonyl-4,4′-dibromobiphenyl was synthesized by amethod described in Journal of the American Chemical Society (1956), 78,3196-3198.

Synthesis Example 8 Synthesis of Compound MM-Y

In a 3 L-three neck flask, compound MM-X (264 g) synthesized above wasweighed, dissolved in dichloromethane (900 ml) and purged with nitrogen.This solution was cooled to 0° C. or less and a boron trifluoridediethyl ether complex (245 ml) was added dropwise while the temperaturewas kept at 5° C. or less. After the solution was slowly increased toroom temperature, it was stirred overnight. This reaction solution waspoured in a 2 L of ice water while stirring and stirred for 30 minutes.The layers were separated and the water layer was extracted with 100 mlof dichloromethane. Organic layers were combined and a 10% aqueouspotassium phosphate solution (1 L) was added and then layers wereseparated. The organic layer was washed twice with water (1 L), driedover magnesium sulfate and then the solvent was distilled away. Theresultant oil was dissolved in 200 ml of toluene and passed through aglass filter lined with silica gel to filtrate. After the solvent wasdistilled away, 500 ml of methanol was added and vigorously stirred. Theresultant crystal was filtrated and washed with methanol.Recrystallization was performed from a solvent mixture of hexane/butylacetate to obtain compound MM-Y (121 g).

¹H-NMR (300 MHz, CDCl₃); δ0.86 (6H, t), 1.26 (12H, m), 1.52 (4H, m),2.51 (4H, t), 6.87 (2H, d), 7.00 (2H, s), 7.04 (2H, d), 7.12 (2H, t),7.46 (2H, dd), 7.48 (2H, d), 7.55 (2H, d) ppm.

Synthesis Example 9 Synthesis of Compound MM-5

In a 2 L three-neck flask, compound MM-Y (50 g) was weighted and purgedwith nitrogen. Dewatered THF (500 ml) was added and cooled to −70° C. orless. While the solution was kept at −70° C. or less, a 2.5 M n-butyllithium/hexane solution (68 ml) was added dropwise. After dropwiseaddition, the solution was stirred for 4 hours while keeping thetemperature. 2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (44ml) was added and then the solution was slowly increased to roomtemperature and stirred overnight. The solution was cooled to −30° C.and a 2 M hydrochloric acid/diethyl ether solution (78 ml) was addeddropwise thereto and then the temperature of the solution was increasedto room temperature. After the solvent was distilled away, the resultantsubstance was dissolved by adding toluene (400 ml) and filtrated bypassing it through a glass filter lined with silica gel. When thesolvent of the resultant solution was distilled away to obtain a crudeproduct (50 g). Under a nitrogen atmosphere, recrystallization wasperformed from a toluene/acetonitrile solvent to obtain 34 g of compoundMM-5.

¹H-NMR (300 MHz, CDCl₃); δ0.86 (6H, t), 1.26-1.29 (12H, m), 1.31 (24H,s), 1.52-1.53 (4H, m), 2.50 (4H, t), 6.92 (2H, d), 7.00 (2H, d), 7.08(2H, t), 7.13 (2H, s), 7.77 (2H, d), 7.81-7.82 (4H, m) ppm.

Example 6 Synthesis of Polymer Compound P-1

Under an inert gas atmosphere,2,7-bis(1,3,2-dioxaborolan-2-yl)-9,9-dioctylfluorene (1.06 g),2,7-dibromo-9,9-dioctylfluorene (0.22 g),bis(4-bromophenyl)-(4-sec-butylphenyl)-amine (0.55 g), compound M-4(0.20 g), bis triphenylphosphine palladium dichloride (1.4 mg),trioctylmethylammonium chloride (trade name: Aliquat 336, manufacturedby Aldrich) (0.25 g) and toluene (40 ml) were blended and heated to 105°C. To the resultant reaction solution, a 2 M aqueous sodium carbonatesolution (6 ml) was added dropwise and refluxed for 15 hours. Aftercompletion of the reaction, phenylboric acid (240 mg) was added andrefluxed for further 4 hours. Subsequently, to this, a 1.8 M aqueoussodium diethyldithiacarbamate solution (10 ml) was added and stirred at80° C. for 4 hours. The resultant reaction solution was cooled to roomtemperature, then washed three times with water (30 ml), three timeswith a 3 wt % aqueous acetic acid solution (30 ml) and three times withwater (30 ml), and purified by passing it through an alumina column anda silica gel column. The resultant toluene solution was added dropwiseto methanol (300 ml) and stirred for one hour. Thereafter, the resultantsolid substance was filtrated and dried to obtain polymer compound P-1(0.7 g) represented by the following formula:

wherein the numbers attached outside parentheses each represent a molarratio of a repeating unit.

The polystyrene-equivalent number average molecular weight of polymercompound P-1 was 1.1×10⁵ and the polystyrene-equivalent weight averagemolecular weight thereof was 3.8×10⁵.

Note that bis(4-bromophenyl)-(4-sec-butylphenyl)-amine was synthesizedby a method described in WO2002/045184.

Example 7 Synthesis of Polymer Compound P-2

Under an inert gas atmosphere,2,7-bis(1,3,2-dioxaborolan-2-yl)-9,9-dioctylfluorene (1.05 g),2,7-dibromo-9,9-dioctylfluorene (0.77 g), compound M-4 (0.31 g), bistriphenylphosphine palladium dichloride (1.4 mg), trioctylmethylammoniumchloride (trade name: Aliquat 336, manufactured by Aldrich) (0.25 g) andtoluene (40 ml) were blended and heated to 105° C. To the resultantreaction solution, a 2 M aqueous sodium carbonate solution (6 ml) wasadded dropwise and refluxed for 20 hours. After completion of thereaction, to this, phenylboric acid (240 mg) was added and refluxed forfurther 4 hours. Subsequently, to this, a 1.8 M aqueous sodiumdiethyldithiacarbamate solution (10 ml) was added and stirred at 80° C.for 4 hours. The resultant reaction solution was cooled to roomtemperature, then washed three times with water (30 ml), three timeswith a 3 wt % aqueous acetic acid solution (30 ml) and three times withwater (30 ml), and purified by passing it through an alumina column anda silica gel column. The resultant toluene solution was added dropwiseto methanol (300 ml) and stirred for one hour. Thereafter, the resultantsolid substance was filtrated and dried to obtain polymer compound P-2(0.8 g) represented by the following formula:

wherein the numbers attached outside parentheses each represent a molarratio of a repeating unit.

The polystyrene-equivalent number average molecular weight of polymercompound P-2 was 4.1×10⁴ and the polystyrene-equivalent weight averagemolecular weight thereof was 1.3×10⁵.

Example 8 Synthesis of Polymer Compound P-3

Under an inert gas atmosphere,2,7-bis(1,3,2-dioxaborolan-2-yl)-9,9-dioctylfluorene (1.06 g),2,7-dibromo-9,9-dioctylfluorene (0.66 g),N,N′-bis-(4-bromophenyl)-bis-(4-butylphenyl)-p-phenylenediamine (0.14g), compound M-4 (0.20 g), compound MM-1 (0.09 g), palladium acetate(0.4 mg), tris(o-methoxyphenyl)phosphine (2.8 mg),trioctylmethylammonium chloride (trade name: Aliquat 336, manufacturedby Aldrich) (0.25 g) and toluene (40 ml) were blended and heated to 105°C. To the resultant reaction solution, a 2 M aqueous sodium carbonatesolution (11 ml) was added dropwise and refluxed for 18 hours. Aftercompletion of the reaction, to this, phenylboric acid (240 mg) was addedand refluxed for further 4 hours. Subsequently, to this, a 1.8 M aqueoussodium diethyldithiacarbamate solution (10 ml) was added and stirred at80° C. for 4 hours. The resultant reaction solution was cooled to roomtemperature, then washed three times with water (30 ml), three timeswith a 3 wt % aqueous acetic acid solution (30 ml) and three times withwater (30 ml), and purified by passing it through an alumina column anda silica gel column. The resultant toluene solution was added dropwiseto methanol (300 ml) and stirred for one hour. Thereafter, the resultantsolid substance was filtrated and dried to obtain polymer compound P-3(0.7 g) represented by the following formula:

wherein the numbers attached outside parentheses each represent a molarratio of a repeating unit.

The polystyrene-equivalent number average molecular weight of polymercompound P-3 was 1.2×10⁵ and the polystyrene-equivalent weight averagemolecular weight thereof was 3.9×10⁵.

Example 9 Synthesis of Polymer Compound P-4

Under an inert gas atmosphere,2,7-bis(1,3,2-dioxaborolan-2-yl)-9,9-dioctylfluorene (1.05 g),2,7-dibromo-9,9-dioctylfluorene (0.55 g), compound MM-4 (0.55 g)represented by the following formula (MM-4):

compound M-5 (0.09 g), palladium acetate (0.4 mg),tris(o-methoxyphenyl)phosphine (2.8 mg), trioctylmethylammonium chloride(trade name: Aliquat 336, manufactured by Aldrich) (0.25 g) and toluene(40 ml) were blended and heated to 105° C. To the resultant reactionsolution, a 2 M aqueous sodium carbonate solution (11 ml) was addeddropwise and refluxed for 22 hours. After completion of the reaction, tothis, phenylboric acid (240 mg) was added and refluxed for further 4hours. Subsequently, to this, a 1.8 M aqueous sodiumdiethyldithiacarbamate solution (10 ml) was added and stirred at 80° C.for 4 hours. The resultant reaction solution was cooled to roomtemperature, then washed three times with water (30 ml), three timeswith a 3 wt % aqueous acetic acid solution (30 ml) and three times withwater (30 ml), and purified by passing it through an alumina column anda silica gel column. The resultant toluene solution was added dropwiseto methanol (300 ml) and stirred for one hour. Thereafter, the resultantsolid substance was filtrated and dried to obtain polymer compound P-5(0.7 g) represented by the following formula:

wherein the numbers attached outside parentheses each represent a molarratio of a repeating unit.

The polystyrene-equivalent number average molecular weight of polymercompound P-5 was 4.2×10⁴ and the polystyrene-equivalent weight averagemolecular weight thereof was 7.5×10⁴.

Note that compound MM-4 was synthesized by a method described inEP1310539.

Example 10 Synthesis of Polymer Compound P-5

Under an inert gas atmosphere,2,7-bis(1,3,2-dioxaborolan-2-yl)-9,9-dioctylfluorene (1.06 g),2,7-dibromo-9,9-dioctylfluorene (0.66 g), compound M-7 (0.55 g),palladium acetate (0.4 mg), tris(o-methoxyphenyl)phosphine (2.8 mg),trioctylmethylammonium chloride (trade name: Aliquat 336, manufacturedby Aldrich) (0.25 g) and toluene (40 ml) were blended and heated to 105°C. To the resultant reaction solution, a 2 M aqueous sodium carbonatesolution (11 ml) was added dropwise and refluxed for 4 hours. Aftercompletion of the reaction, to this, phenylboric acid (240 mg) was addedand refluxed for further 4 hours. Subsequently, to this, a 1.8 M aqueoussodium diethyldithiacarbamate solution (10 ml) was added and stirred at80° C. for 4 hours. The resultant reaction solution was cooled to roomtemperature, then washed three times with water (30 ml), three timeswith a 3 wt % aqueous acetic acid solution (30 ml) and three times withwater (30 ml), and purified by passing it through an alumina column anda silica gel column. The resultant toluene solution was added dropwiseto methanol (300 ml) and stirred for one hour. Thereafter, the resultantsolid substance was filtrated and dried to obtain polymer compound P-6(0.9 g) represented by the following formula:

wherein the numbers attached outside parentheses each represent a molarratio of a repeating unit.

The polystyrene-equivalent number average molecular weight of polymercompound P-6 was 1.0×10⁵ and the polystyrene-equivalent weight averagemolecular weight thereof was 3.9×10⁵.

Example 11 Synthesis of Polymer Compound P-6

Under an inert gas atmosphere, the compound (1.48 g) represented by thefollowing formula (MM-5):

2,7-dibromo-9,9-dioctylfluorene (0.22 g), the compound (0.82 g)represented by the above formula (MM-4), compound (M-9) (0.23 g),palladium acetate (0.4 mg), tris(o-methoxyphenyl)phosphine (2.8 mg) andtoluene (44 ml) were blended and heated to 105° C. To the resultantreaction solution, a 20% aqueous tetraethyl ammonium hydroxide solution(6.6 ml) was added dropwise and refluxed for 4 hours. After completionof the reaction, to this, phenylboric acid (240 mg) was added andrefluxed for further 18 hours. Subsequently, to this, a 1.8 M aqueoussodium diethyldithiacarbamate solution (22 ml) was added and stirred at80° C. for 4 hours. The resultant reaction solution was cooled to roomtemperature, then washed three times with water (30 ml), three timeswith a 3 wt % aqueous acetic acid solution (30 ml) and three times withwater (30 ml), and purified by passing it through an alumina column anda silica gel column. The resultant toluene solution was added dropwiseto methanol (300 ml) and stirred for one hour and thereafter, theresultant solid substance was filtrated and dried to obtain polymercompound P-6 (1.5 g) represented by the following formula:

wherein the numbers attached outside parentheses each represent a molarratio of a repeating unit.

The polystyrene-equivalent number average molecular weight of polymercompound P-6 was 2.2×10⁵ and the polystyrene-equivalent weight averagemolecular weight thereof was 8.5×10⁵.

Example 12 Synthesis of Polymer Compound P-7

Under an inert gas atmosphere, the compound (1.48 g) represented by theabove formula (MM-5), 2,7-dibromo-9,9-dioctylfluorene (0.22 g), thecompound (0.82 g) represented by the above formula (MM-4), compound(M-4) (0.20 g), palladium acetate (0.4 mg),tris(o-methoxyphenyl)phosphine (2.8 mg) and toluene (44 ml) were blendedand heated to 105° C. To the resultant reaction solution, a 20% aqueoustetraethyl ammonium hydroxide solution (6.6 ml) was added dropwise andrefluxed for 18 hours. After completion of the reaction, to this,phenylboric acid (240 mg) was added and refluxed for further 4 hours.Subsequently, to this, a 1.8 M aqueous sodium diethyldithiacarbamatesolution (22 ml) was added and stirred at 80° C. for 4 hours. Theresultant reaction solution was cooled to room temperature, then washedthree times with water (30 ml), three times with a 3 wt % aqueous aceticacid solution (30 ml) and three times with water (30 ml), and purifiedby passing it through an alumina column and a silica gel column. Theresultant toluene solution was added dropwise to methanol (300 ml) andstirred for one hour and thereafter, the resultant solid substance wasfiltrated and dried to obtain polymer compound P-7 (1.3 g) representedby the following formula:

wherein the numbers attached outside parentheses each represent a molarratio of a repeating unit.

The polystyrene-equivalent number average molecular weight of polymercompound P-7 was 5.1×10⁴ and the polystyrene-equivalent weight averagemolecular weight thereof was 1.0×10⁵.

Comparative Example 1 Synthesis of Polymer Compound CP-1

Under an inert gas atmosphere,2,7-bis(1,3,2-dioxaborolan-2-yl)-9,9-dioctylfluorene (1.06 g),bis(4-bromophenyl)-(4-sec-butylphenyl)-amine (0.87 g), compound MM-6(0.04 g) represented by the following formula (MM-6):

bis triphenylphosphine palladium dichloride (1.4 mg),trioctylmethylammonium chloride (trade name: Aliquat 336, manufacturedby Aldrich) (0.25 g) and toluene (40 ml) were blended and heated to 105°C. To the resultant reaction solution, a 2 M aqueous sodium carbonatesolution (6 ml) was added dropwise and refluxed for 7 hours.After completion of the reaction, to this, phenylboric acid (240 mg) wasadded and refluxed for further 4 hours. Subsequently, to this, a 1.8 Maqueous sodium diethyldithiacarbamate solution (10 ml) was added andstirred at 80° C. for 4 hours. The resultant reaction solution wascooled to room temperature, then washed three times with water (30 ml),three times with a 3 wt % aqueous acetic acid solution (30 ml) and threetimes with water (30 ml), and purified by passing it through an aluminacolumn and a silica gel column. The resultant toluene solution was addeddropwise to methanol (300 ml) and stirred for one hour. Thereafter, theresultant solid substance was filtrated and dried to obtain polymercompound CP-1 (0.8 g) represented by the following formula:

wherein the numbers attached outside parentheses each represent a molarratio of a repeating unit.

The polystyrene-equivalent number average molecular weight of polymercompound CP-1 was 3.4×10⁴ and the polystyrene-equivalent weight averagemolecular weight thereof was 6.7×10⁴.

Note that compound MM-6 was synthesized by a method described inUS2004/035221.

Comparative Example 2 Synthesis of Polymer Compound CP-2

Under an inert gas atmosphere,2,7-bis(1,3,2-dioxaborolan-2-yl)-9,9-dioctylfluorene (1.06 g),2,7-dibromo-9,9-dioctylfluorene (0.22 g),bis(4-bromophenyl)-(4-sec-butylphenyl)-amine (0.55 g), compound MM-2(0.21 g) represented by the following formula (MM-2):

bis triphenylphosphine palladium dichloride (1.4 mg),trioctylmethylammonium chloride (trade name: Aliquat 336, manufacturedby Aldrich) (0.25 g) and toluene (40 ml) were blended and heated to 105°C. To the resultant reaction solution, a 2 M aqueous sodium carbonatesolution (6 ml) was added dropwise and refluxed for 7 hours. Aftercompletion of the reaction, to this, phenylboric acid (240 mg) was addedand refluxed for further 4 hours. Subsequently, to this, a 1.8 M aqueoussodium diethyldithiacarbamate solution (10 ml) was added and stirred at80° C. for 4 hours. The resultant reaction solution was cooled to roomtemperature, then washed three times with water (30 ml), three timeswith a 3 wt % aqueous acetic acid solution (30 ml) and three times withwater (30 ml) and purified by passing it through an alumina column and asilica gel column. The resultant toluene solution was added dropwise tomethanol (300 ml) and stirred for one hour. Thereafter, the resultantsolid substance was filtrated and dried to obtain polymer compound CP-2(yield 0.9 g) represented by the following formula:

wherein the numbers attached outside parentheses each represent a molarratio of a repeating unit.

The polystyrene-equivalent number average molecular weight of polymercompound CP-2 was 8.4×10⁴ and the polystyrene-equivalent weight averagemolecular weight thereof was 2.0×10⁵.

Note that compound MM-2 was synthesized by a method described in JP2008-106241 A.

Comparative Example 3 Synthesis of Polymer Compound CP-3

Under an inert gas atmosphere,2,7-bis(1,3,2-dioxaborolan-2-yl)-9,9-dioctylfluorene (1.06 g), compoundMM-3 (0.22 g) represented by the above formula MM-3,N,N-di(4-bromophenyl)aniline (0.73 g), bis triphenylphosphine palladiumdichloride (1.4 mg), trioctylmethylammonium chloride (trade name:Aliquat 336, manufactured by Aldrich) (0.25 g) and toluene (40 ml) wereblended and heated to 105° C. To the resultant reaction solution, a 2 Maqueous sodium carbonate solution (6 ml) was added dropwise and refluxedfor 20 hours. After completion of the reaction, phenylboric acid (240mg) was added and refluxed for further 4 hours. Subsequently, a 1.8 Maqueous sodium diethyldithiacarbamate solution (10 ml) was added andstirred at 80° C. for 4 hours. The resultant reaction solution wascooled to room temperature, then washed three times with water (30 ml),three times with a 3 wt % aqueous acetic acid solution (30 ml) and threetimes with water (30 ml) and purified by passing it through an aluminacolumn and a silica gel column. The resultant toluene solution was addeddropwise to methanol (300 ml) and stirred for one hour and thereafter,the resultant solid substance was filtrated and dried to obtain polymercompound CP-3 (0.8 g) represented by the following formula:

wherein the numbers attached outside parentheses each represent a molarratio of a repeating unit.

The polystyrene-equivalent number average molecular weight of polymercompound CP-3 was 5.3×10⁴ and the polystyrene-equivalent weight averagemolecular weight thereof was 1.9×10⁵.

Synthesis Example 10 Synthesis of Polymer Compound P-8

Under an inert gas atmosphere, compound MM-8 (7.28 g) represented by thefollowing formula MM-8:

2,7-dibromo-9,9-dioctylfluorene (4.94 g), compound MM-9 (0.74 g),represented by the following formula MM-9:

bis triphenylphosphine palladium dichloride (7.0 mg),trioctylmethylammonium chloride (trade name: Aliquat 336, manufacturedby Aldrich) (1.30 g) and toluene (100 ml) were blended and heated to105° C. To the resultant reaction solution, a 2 M aqueous sodiumcarbonate solution (27 ml) was added dropwise and refluxed for 2 hours.After completion of the reaction, phenylboric acid (120 mg) was addedand refluxed for further 4 hours. Subsequently, a 1.8 M aqueous sodiumdiethyldithiacarbamate solution (60 ml) was added and stirred at 80° C.for 4 hours. The resultant reaction solution was cooled to roomtemperature, then washed three times with water (130 ml), three timeswith a 3 wt % aqueous acetic acid solution (130 ml) and three times withwater (130 ml) and purified by passing it through an alumina column anda silica gel column. The resultant toluene solution was added dropwiseto methanol (1.5 L) and stirred for one hour. Thereafter, the resultantsolid substance was filtrated and dried to obtain polymer compound P-8(8.0 g) represented by the following formula:

wherein the numbers attached outside parentheses each represent a molarratio of a repeating unit.

The polystyrene-equivalent number average molecular weight of polymercompound P-8 was 5.1×10⁴ and the polystyrene-equivalent weight averagemolecular weight thereof was 1.4×10⁵.

Note that compound MM-8 represented by the above formula MM-8 wassynthesized by a method described in WO2008111658.

Furthermore, compound MM-9 represented by the above formula MM-9 wassynthesized by a method described in EP1394188.

<Preparation of Liquid Composition>

Compound M-7, polymer compounds P-1 to P-7 and polymer compounds CP-1 toCP-3 were each dissolved in xylene. In this manner, a liquid compositioncontaining about 1 wt % of each of the compounds was prepared.

<Evaluation of Residual Film Rate on Glass Substrate>

The liquid composition was added dropwise onto a glass substrate by aspin coater (trade name: MS-A100 type, manufactured by Misawa) in thecondition of 1000 rpm for 15 seconds. The film thickness (H₁) of theresultant film was measured by a profiler (trade name: P-16+,manufactured by KLA-Tencor Corporation).

Subsequently, in a globe box purged with nitrogen, the film on the glasssubstrate was baked by use of a high power hot plate (trade name:HP-ISA, manufactured by AS ONE Corporation), at a baking temperatureshown in Table 1 for 20 minutes. The resultant film on the glasssubstrate was cooled to room temperature, then soaked in a xylenesolution and then rinsed by a spin coater (trade name: MS-A100 type,manufactured by Misawa) in the conditions of 1000 rpm for 15 seconds.The film thickness (H₂) of the film produced was measured by theprofiler (trade name: P-16+, manufactured by KLA-Tencor Corporation).

A value of (H₂)/(H₁) was defined as a residual film rate and the resultsobtained are shown in Table 1.

TABLE 1 Residual film rate 130° C. 150° C. 170° C. 190° C. Compound BakeBake Bake Bake Example 13 M-7 44% 54% 84% 99% Example 14 P-1 96% 96% 99%99% Example 15 P-2 74% 88% 92% 96% Example 16 P-3 83% 85% 96% 97%Example 17 P-4 22% 38% 52% 74% Example 18 P-5 59% 68% 82% 89% Example 19P-6 74% 90% 98% 99% Example 20 P-7 63% 87% 91% 99% Comparative CP-1 0%0% 0% 10% Example 4 Comparative CP-2 0% 0% 0% 53% Example 5 ComparativeCP-3 0% 0% 38% 51% Example 6

<Evaluation>

Compound M-7 and polymer compounds P-1 to P-7 were each confirmed tohave high harden ability compared to polymer compounds CP-1 to CP-3.Furthermore, even in the range as low as 130° C. to 150° C. compared to190° C., compound M-7 and polymer compounds P-1 to P-7 exhibited hardenability.

Production and Evaluation of Electroluminescence (EL) Device Example 21Preparation of Polymer Compound <P-5> Solution

The polymer compound <P-5> obtained above was dissolved in xylene toprepare a xylene solution having a polymer concentration of 1.2 wt %.

Preparation of Polymer Compound <P-8> Solution

The polymer compound <P-8> obtained above was dissolved in xylene toprepare a xylene solution having a polymer concentration of 1.2 wt %.

Production of EL Device

On a glass substrate to which an ITO film of 150 nm in thickness wasattached by a sputtering method, a suspension solution ofpoly(3,4)ethylenedioxythiophene/polystyrene sulfonate (Baytron P AI4083manufactured by Bayer) previously filtrated by a 0.2 μm membrane filter,was applied by spin coating to form a film of 70 nm in thickness anddried on a hot plate at 200° C. for 10 minutes. Subsequently, using axylene solution of the polymer compound <P-5> obtained above, a film wasformed by spin coating at a rotation rate of 1600 rpm and heated on ahot plate at 150° C. for 20 minutes to harden the film. After completionof film formation, the thickness of the film was about 20 nm.Furthermore, using a xylene solution of the polymer compound <P-8>obtained above, a film was formed by spin coating at a rotation rate of1500 rpm. After the film formation, the thickness of the film was about60 nm. Furthermore, this was dried under reduced pressure at 130° C. for10 minutes, and thereafter barium was vapor-deposited as a cathode in athickness of about 5 nm, and then aluminum was vapor-deposited in athickness of about 100 nm to produce an EL device. Note that vapordeposition of a metal was initiated after a degree of vacuum reached1×10⁻⁴ Pa or less.

Performance of EL Device

When voltage was applied to the resultant device, EL emission having apeak at 460 nm was provided from the device.

The time (life) for reducing a degree of brightness from the initialbrightness (100 cd/m²) to a half (50%) was as long as 26 hours.

Example 22 Preparation of Polymer Compound <P-6> Solution

The polymer compound <P-6> obtained above was dissolved in xylene toprepare a xylene solution having a polymer concentration of 1.2 wt %.

Preparation of Polymer Compound <P-8> Solution

The polymer compound <P-8> obtained above was dissolved in xylene toprepare a xylene solution having a polymer concentration of 1.2 wt %.

Production of EL Device

On a glass substrate to which an ITO film of 150 nm in thickness wasattached by a sputtering method, a suspension solution ofpoly(3,4)ethylenedioxythiophene/polystyrene sulfonate (Baytron P AI4083manufactured by Bayer) previously filtrated by a 0.2 μm membrane filter,was applied by spin coating to form a film of 70 nm in thickness anddried on a hot plate at 200° C. for 10 minutes. Subsequently, using axylene solution of the polymer compound <P-6> obtained above, a film wasformed by spin coating at a rotation rate of 1600 rpm and heated on ahot plate at 150° C. for 20 minutes to harden the film. After the filmformation, the thickness of the film was about 20 nm. Furthermore, usinga xylene solution of the polymer compound <P-8> obtained above, a filmwas formed by spin coating at a rotation rate of 1500 rpm. Aftercompletion of film formation, the thickness of the film was about 60 nm.Furthermore, this was dried under reduced pressure at 130° C. for 10minutes, and thereafter barium was vapor-deposited as a cathode in athickness of about 5 nm, and then aluminum was vapor-deposited in athickness of about 100 nm to produce an EL device. Note that vapordeposition of a metal was initiated after a degree of vacuum reached1×10⁻⁴ Pa or less.

Performance of EL Device

When voltage was applied to the resultant device, EL emission having apeak at 470 nm was provided from the device.

The time (life) for reducing a degree of brightness from the initialbrightness (100 cd/m²) to a half (50%) was as long as 22 hours.

Comparative Example 7 Preparation of Polymer Compound <CP-1> Solution

The polymer compound <CP-1> obtained above was dissolved in xylene toprepare a xylene solution having a polymer concentration of 1.2 wt %.

Production of EL Device

On a glass substrate to which an ITO film of 150 nm in thickness wasattached by a sputtering method, a suspension solution ofpoly(3,4)ethylenedioxythiophene/polystyrene sulfonate (Baytron P AI4083manufactured by Bayer) previously filtrated by a 0.2 μm membrane filterwas applied by spin coating to form a film of 70 nm in thickness anddried on a hot plate at 200° C. for 10 minutes. Subsequently, using axylene solution of the polymer compound <CP-1> obtained above, a filmwas formed by spin coating at a rotation rate of 1600 rpm and heated ona hot plate at 150° C. for 20 minutes to harden the film. Aftercompletion of film formation, the thickness of the film was about 20 nm.Furthermore, using a xylene solution of the polymer compound <P-8>obtained above, a film was formed by spin coating at a rotation rate of1500 rpm. After the film formation, the thickness of the film was about60 nm. Furthermore, this was dried under reduced pressure at 130° C. for10 minutes, and thereafter barium was vapor-deposited as a cathode in athickness of about 5 nm, and then aluminum was vapor-deposited in athickness of about 100 nm to produce an EL device. Note that vapordeposition of a metal was initiated after a degree of vacuum reached1×10⁻⁴ Pa or less.

Performance of EL Device

When voltage was applied to the resultant device, EL emission having apeak at 460 nm was provided from the device.

The time (life) for reducing a degree of brightness from the initialbrightness (100 cd/m²) to a half (50%) was one hour.

Comparative Example 8 Preparation of Polymer Compound <CP-2> Solution

The polymer compound <CP-2> obtained above was dissolved in xylene toprepare a xylene solution having a polymer concentration of 1.2 wt %.

Production of EL Device

On a glass substrate to which an ITO film of 150 nm in thickness wasattached by a sputtering method, a suspension solution ofpoly(3,4)ethylenedioxythiophene/polystyrene sulfonate (Baytron P AI4083manufactured by Bayer) previously filtrated by a 0.2 μm membrane filterwas applied by spin coating to form a film of 70 nm in thickness anddried on a hot plate at 200° C. for 10 minutes. Subsequently, using axylene solution of the polymer compound <CP-2> obtained above, a filmwas formed by spin coating at a rotation rate of 1600 rpm and heated ona hot plate at 150° C. for 20 minutes to harden the film. Aftercompletion of film formation, the thickness of the film was about 20 nm.Furthermore, using a xylene solution of the polymer compound <P-8>obtained above, a film was formed by spin coating at a rotation rate of1500 rpm. After the film formation, the thickness of the film was about60 nm. Furthermore, this was dried under reduced pressure at 130° C. for10 minutes, and thereafter barium was vapor-deposited as a cathode in athickness of about 5 nm, and then aluminum was vapor-deposited in athickness of about 100 nm to produce an EL device. Note that vapordeposition of a metal was initiated after a degree of vacuum reached1×10⁻⁴ Pa or less.

Performance of EL Device

When voltage was applied to the resultant device, EL emission having apeak at 460 nm was provided from the device.

The time (life) for reducing a degree of brightness from the initialbrightness (100 cd/m²) to a half (50%) was 14 hours.

Comparative Example 9 Preparation of Polymer Compound <CP-3> Solution

The polymer compound <CP-3> obtained above was dissolved in xylene toprepare a xylene solution having a polymer concentration of 1.2 wt %.

Production of EL Device

On a glass substrate to which an ITO film of 150 nm in thickness wasattached by a sputtering method, a suspension solution ofpoly(3,4)ethylenedioxythiophene/polystyrene sulfonate (Baytron P AI4083manufactured by Bayer) filtrated by a 0.2 μm membrane filter was appliedby spin coating to form a film of 70 nm in thickness and dried on a hotplate at 200° C. for 10 minutes. Subsequently, using a xylene solutionof the polymer compound <CP-3> obtained above, a film was formed by spincoating at a rotation rate of 1600 rpm and heated on a hot plate at 150°C. for 20 minutes to harden the film. After completion of filmformation, the thickness of the film was about 20 nm. Furthermore, usinga xylene solution of the polymer compound <P-8> obtained above, a filmwas formed by spin coating at a rotation rate of 1500 rpm. Aftercompletion of film formation, the thickness of the film was about 60 nm.Furthermore, this was dried under reduced pressure at 130° C. for 10minutes, and thereafter barium was vapor-deposited as a cathode in athickness of about 5 nm, and then aluminum was vapor-deposited in athickness of about 100 nm to produce an EL device. Note that vapordeposition of a metal was initiated after a degree of vacuum reached1×10⁻⁴ Pa or less.

Performance of EL Device

When voltage was applied to the resultant device, EL emission having apeak at 460 nm was provided from the device.

The time (life) for reducing a degree of brightness from the initialbrightness (100 cd/m²) to a half (50%) was 11 hours.

INDUSTRIAL APPLICABILITY

A compound containing a 1,3-diene structure of the present invention canbe used as a material and the like for use in an organic layer of alight-emitting device.

1. A compound comprising a divalent group represented by the followingformula (I):

wherein Ar¹ represents an arylene group, a divalent heterocyclic groupor a divalent aromatic amine group; J¹ represents a phenylene group; J²represents an alkylene group; X represents an oxygen atom or a sulfuratom; j is 0 or 1, k is an integer of 0 to 3 and l is 0 or 1, such that1≦j+k+l≦5; m is 1 or 2; R¹ represents a hydrogen atom, an alkyl group,an alkoxy group, an alkylthio group, an aryl group, an aryloxy group, anarylthio group, an arylalkyl group, an arylalkoxy group, anarylalkylthio group, an arylalkenyl group, an arylalkynyl group, anamino group, a substituted amino group, a silyl group, a substitutedsilyl group, a halogen atom, an acyl group, an acyloxy group, an imineresidue, a carbamoyl group, an acid imide group, a monovalentheterocyclic group, a carboxyl group, a substituted carboxyl group, acyano group or a nitro group; a plurality of R¹ may be the same ordifferent; and a plurality of J¹, J², X, j, k and l each may be the sameor different.
 2. The compound according to claim 1, wherein j is
 1. 3.The compound according to claim 1, wherein R¹ is a hydrogen atom, analkyl group, an alkoxy group, a halogen atom, a nitro group or a cyanogroup.
 4. The compound according to claim 1, wherein Ar¹ is a phenylenegroup or a fluorene-diyl group.
 5. The compound according to claim 1,wherein Ar¹ is a divalent group represented by the following formula(II):

wherein Y represents an oxygen atom, a sulfur atom, —N(R²²)—,—O—C(R²³)(R²⁴)—, or —Si(R²⁵)(R²⁶)—; R²², R²³, R²⁴, R²⁵ and R²⁶ eachindependently represent a hydrogen atom, an alkyl group, an alkoxygroup, an aryl group or an arylalkyl group; and the formula may have asubstituent.
 6. The compound according to claim 1, wherein Ar¹ is adivalent group represented by the following formula (III):

wherein R³ represents a hydrogen atom, an alkyl group, an alkoxy groupor a substituted amino group; five R³ may be the same or different, or adivalent group represented by the following formula (IV):

wherein R⁴ represents a hydrogen atom, an alkyl group, an alkoxy groupor a substituted amino group; and ten R⁴ may be the same or different.7. The compound according to claim 1, wherein in the above formula (I),a group represented by the following formula (Ia):

wherein j, k, l, J¹, J² and R¹ are the same as defined above, is a grouprepresented by the following formula (Ib):

wherein k, l, J² and R¹ are the same as defined above.
 8. The compoundaccording to claim 8, wherein the group represented by the above formula(Ib) is a group represented by the following formula (Ic):

wherein k, l and J² are the same as defined above, or a grouprepresented by the following formula (Id):

wherein k, l and J² are the same as defined above.
 9. The compoundaccording to claim 1, wherein the compound having a divalent grouprepresented by the above formula (I) is a polymer compound having adivalent group represented by the above formula (I) as a repeating unit.10. The compound according to claim 9, further comprising a repeatingunit represented by the following formula (A):

wherein Ar² represents an arylene group, a divalent heterocyclic groupor a divalent aromatic amine group; J³ represents a direct bond, analkylene group or a phenylene group; n represents 1 or 2; a plurality ofJ³ may be the same or different.
 11. The compound according to claim 10,wherein Ar² is an arylene group, J³ is a direct bond and n is
 2. 12. Thecompound according to claim 9, further comprising a repeating unitrepresented by the following formula (B):

wherein Ar³ represents an arylene group, a divalent heterocyclic groupor a divalent aromatic amine group; J⁴ represents a direct bond, analkylene group or a phenylene group; R⁵ represents a hydrogen atom, analkyl group, an alkoxy group, an alkylthio group, an aryl group, anaryloxy group, an arylthio group, an arylalkyl group, an arylalkoxygroup, an arylalkylthio group, an arylalkenyl group, an arylalkynylgroup, an amino group, a substituted amino group, a silyl group, asubstituted silyl group, a halogen atom, an acyl group, an acyloxygroup, an imine residue, a carbamoyl group, an acid imide group, amonovalent heterocyclic group, a carboxyl group, a substituted carboxylgroup, a cyano group or a nitro group; o represents 1 or 2; a pluralityof R⁵ may be the same or different; and a plurality of J⁴ may be thesame or different.
 13. The compound according to claim 12, wherein Ar³is an arylene group, J⁴ is an alkylene group, and o is
 2. 14. Thecompound according to claim 9, further comprising a repeating unitrepresented by the following formula (C):

wherein R⁶ represents an alkyl group, an aryl group, an arylalkyl groupor an arylalkoxy group; and two R⁶ may be the same or different.
 15. Thecompound according to claim 14, wherein R⁶ is an alkyl group, an arylgroup or an arylalkyl group.
 16. The compound according to claim 9,having a polystyrene-equivalent number average molecular weight of 1×10³to 1×10⁸.
 17. A composition comprising at least one selected from thegroup consisting of a hole transport material, an electron transportmaterial and a light-emitting material and the compound according toclaim
 1. 18. A liquid composition containing the compound according toclaim 1 and a solvent.
 19. A film containing the compound according toclaim
 1. 20. A film obtained by crosslinking the compound according toclaim
 1. 21. A light-emitting device having electrodes comprising ananode and a cathode and an organic layer formed between the electrodesand containing the compound according to claim
 1. 22. The light-emittingdevice according to claim 21, wherein the organic layer is alight-emitting layer or a charge transport layer.
 23. A surface lightsource comprising the light-emitting device according to claim
 21. 24. Adisplay comprising the light-emitting device according to claim
 21. 25.An organic transistor formed of the compound according to claim
 1. 26.An organic photoelectric transducer formed of the compound according toclaim
 1. 27. A compound represented by the following formula (X):

wherein Ar¹ is an arylene group, a divalent heterocyclic group or adivalent aromatic amine group; J¹ represents a phenylene group; J²represents an alkylene group; X represents an oxygen atom or a sulfuratom; X¹ and X² each independently represent a halogen atom; k is aninteger of 0 to 3, l is 0 or 1, m is 1 or 2; and a plurality of J¹, J²,X, k and l each may be the same or different.
 28. A method for producinga compound represented by the following formula (X):

wherein Ar¹, J¹, J², X, X¹, X², k, l and m are the same as definedabove, comprising reacting, in a base, a compound represented by thefollowing formula (XI):

wherein Ar¹ represents an arylene group, a divalent heterocyclic groupor a divalent aromatic amine group; J¹ represents a phenylene group; Xrepresents an oxygen atom or a sulfur atom; X¹ and X² each independentlyrepresent a halogen atom; k is an integer of 0 to 3, l is 0 or 1 and mis 1 or 2; and a plurality of J¹, X, k and l each may be the same ordifferent, and a compound represented by the following formula (XII):

wherein X³ represents a halogen atom; and J² represents an alkylenegroup.